Autoxidation and Photooxidation of 1,3-Diphenylisobenzofuran:

A Kinetic and Product Study1

Division of Chemistry, National Research Council of Canada, Ottawa, Canada KIA OR9
Received January 20, 1975

JAMES A. HOWARD and G. DAVIDMENDENHALL. Can. J. Chem. 53,2199 (1975).

Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

Photooxidation of 1,3-diphenylisobenzofuran(DPBF) in aromatic solvents at 30" gives a

monomeric peroxide along with minor amounts of o-benzylphenyl benzoate, whereas in CCl,
o-dibenzoylbenzene is the principal reaction product. 1,3-Diphenylisobenzofuran is very
susceptible to autoxidation at this temperature (kP/(2k,)li2= 4 M-'I2 S-li2, k, lo5 M-ls-l,
2k, 5 x loBM-Is-') yielding a polyperoxide (50%) and o-dibenzoylbenzene(35%). Clearly,
N

in the absence of appropriate control experiments, neither rapid disappearance of DPBF nor
production of o-dibenzoylbenzene are sufficient to prove the intermediacy of singlet delta
oxygen during molecular oxygen oxidations.

JAMES A. HOWARD et G. DAVIDMENDENHALL. Can. J. Chem.. 53,2199(1975).

La photo-oxydation du diphknyl-1,3 isobenzofuranne (DPBF) dans les solvants aromatiques
B 30" conduit a un peroxyde monombre ainsi qu'a une faible quantite de benzoate de o-benzyl-
phenyle, tandis que dans le CCI, le produit principal de la reaction est le o-dibenzoylbenzkne.
A cette temperature, le diphenyl-1,3 isobenzofuranne est sensible ti I'autoxidation (k,/(2k,)1/2 =
4 M-li2 S-li2, k, lo5 M-I S-I, 2k, N 5 x loBM-ls-l) ce qui conduit t~un polyperoxyde
For personal use only.

(50%) et au o-dibenzoylbenzbne(35%). Clairement, en I'absence d'un contrBle approprie, ni la

disparition rapide du DPBF ni la production de o-dibenzoylbenz6ne suffisent a demontrer
qu'il se forme un intermediaire oxygbne dans 1'Ctat singulet delta au cours des oxydations par
I'oxygkne molkulaire. [Traduit par le journal]

Introduction appropriate control experiments, on the rapid

1,3-Diphenylisobenzofuran(DPBF) is a popu-
lar substrate for photooxidation studies in the
liquid phase because of the rapidity with which
it reacts with electronically excited singlet delta
oxygen (lA,). There have been several determi-
nations of absolute rate constants for this re-
action and it would appear that the 'best' values
lie in the range 6-8 x 10' M-'s-l (1). It is
generally accepted that '0, undergoes a 1,4-
addition to DPBF to give the endo-peroxide 1
which decomposes at ambient temperature to
give o-dibenzoylbenzene (ODB) (2-7).
7sH5 pHs
DPBF 1 ODB
Chemical evidence for the intermediacy of
'0, during photooxidation is based, with the
'NRCC No. 14661.
'NRCC Postdoctorate Fellow, 1971-1973. Present
address: Battelle, Columbus Laboratories, 505 King
Avenue, Columbus, Ohio 43201.
disappearance of DPBF and/or the production
of ODB.
We have recently conducted a thorough
kinetic and product study of the autoxidation
and photooxidation of DPBF at 30' in the
liquid phase. he results of this work and its
relevance to diagnostic tests for the intermediacy
of singlet oxygen during molecular oxygen oxida-
tions are reported here.
Experimental
1,3-Diphenylisobenzofuran (Aldrich) was purified by
pH5
recrystallization or zone refining. The solvents (CCI,,
CsH,, and tert-butylbenzene) were distilled before use.
Oxygen absorptions were followed with the automatic
recording apparatus described previously (8). All re-
actions were performed in solution at 30'. Autoxidations
were initiated by thermal decomposition of a,u'-azo-
bisisobutyronitrile (AIBN). Photooxidations were carried
out in the presence of the radical scavenger 2,6-di-tert-
butyl-4-methylphenol with light of a h > 500 nm.
Polyperoxides were isolated by slow addition of autoxi-
dized DPBF to n-pentane and yields were determined by
weight. The composition of the polymer depended on
the autoxidation chain length (v). For example, autoxida-
tion of DPBF (0.015 M ) initiated by AIBN (0.036 M),
v = 1300, gave a polyperoxide with a molecular weight
of 1350 50, a m.p. of 127.5-128.S0, and an elemental
 CAN. J. CHEM. VOL. 53. 1975

TABLE1. Kinetic data.for autoxidation of DPBF at 30" and 710 Torr

[DPBF], [AIBN] 10' R, 106(-d[02]/dt)o kpl(2kt)1'2

Of) (M) ( M S-') (Ms-') (M-1/2 S-112)

*Po, = 363 Torr.

Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

tThis ratio was obtained by following the disappearance o f DPBF spectrophotometrically

(b = 413 nm) in the presence of a large excess of oxygen (-lo-' M).

analysis of C = 80.54, H = 4.98, and N = 0.62. Yields DPBF (0.015 M ) in t-butylbenzene containing
of o-dibenzoylbenzene and o-benzoylphenyl benzoate AIBN (0.036 M ) absorbed 0.012 M of 0, to
were determined from the intensities of the carbonyl
absorptions in the i.r. give a polyperoxide (50%) and o-dibenzoyl-
Attempts to prepare an analytically pure sample of benzene (35%). Molecular weight determina-
DPBF endoperoxide were unsuccessful. An elemental tions and elemental analyses indicated that the
analysis of a fraction with a measured molecular weight polymer had structure 2 with n = 4-5. The
+
of 290 10 gave C = 81.1, H = 5.15 whereas the
theoretical analysis is C = 79.4, H = 4.67.
The absolute termination rate constant for autoxida-
tion of DPBF was determined from the steady-state
peroxy radical concentration and the rate of chain
initiation by electron spin resonance techniques (9).
For personal use only.

Results and Discussion

Autoxidation
Le Berre and Ratsimbazafy (10) reported that
the self-initiated autoxidation of DPBF in the
dark at ambient temperatures yielded a poly-
meric peroxide with a molecular weight of 2630.
We found that solutions of DPBF did not absorb
oxygen in the dark in the absence of a free
radical initiator at 30". Kinetic chain lengths
were, however, very long when autoxidation was
initiated by AIBN. Overall rates of autoxidation
were found to fit the general kinetic expression
for hydrocarbon autoxidation
low molecular weight of the polyperoxide rela-
tive to the kinetic chain length is probably the
result of 0-0 bond cleavage during autoxida-
tion, a common characteristic of polymerizable
olefin autoxidation (12). This was supported
by the observation that a sample of polyper-
oxide dissolved in benzene had a half-life of
-72 h at 50" and thermolyzed to give ODB
(1 mol per mol of polymer).

where kp and 2kt are the rate controlling propa-

gation and termination rate constants, Ri is the
rate of chain initiation, and [RH] is the substrate
concentration. Kinetic data for autoxidation are
given in Table 1. The oxidizability of DPBF at
30" is 4 M-'I2 s-li2 and since 2kt is -5 x 10'
M-' s-' the reactivity of DPBF to its own
peroxy radical is -lo5 M-' s- l. Solutions of
DPBF are, therefore, susceptible to autoxida- Photooxidation
tion because of the high reactivity of this sub- Dufraisse and Ecary (13) reported that photo-
strate to peroxy radicals (cf. cyclohexa-1,3-diene oxidation of DPBF yielded a crystalline endo-
which has a homopropagation rate constant of peroxide which was stable for several hours at
800 M-' s-l at 30" (11)). -78" but which exploded when the temperature
 HOWARD AND MENDENIHALL: PHOTOOXIDATION 2201

was raised to 18". We found, however, that the C6H5

I
principal stable photooxidation products at 30"
depend on the nature of the solvent.
In aromatic solvents, such as benzene and
tert-butylbenzene, less than 10% of the reaction
product contained the carbonyl function(s). The
principal product was a white crystalline material
which liberated 1 equiv. of iodine from acidi- Conclusions
fied KI and was reduced to ODB by 1 equiv. of It is quite clear from this work that DPBF
triphenylphosphine. The molecular weight of this can react very rapidly with ground state triplet
Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

material and the stoichiometry of the reaction
were consistent with a 1 : 1 adduct between
oxygen and DPBF. We feel confident that this
compound is the endo-peroxide 1 although ele-
mental analyses were unsatisfactory. Thermal
decomposition of 1 in tert-butylbenzene at 20'
indicated that it had a t,,, of 100 h at this
temperature in this solvent.
The principal minor product was o-benzoyl-
phenyl benzoate which is believed to arise by
0-0 bond cleavage of 1 followed by rearrange-
ment (6).
For personal use only.
oxygen in the presence of a free radical initiator
to give ODB. Great care should, therefore, be
exercised to ensure that the disappearance of
DPBF or the production of ODB during photo-
oxidation is not due to adventitious autoxida-
tion.
We thank Mr. J. H. B. Chenier for assistance with the
experimental work, Mr. H. Seguin for elemental analyses
and molecular weights determinations, a n d a referee for
valuable comments.
1. P. B. MERKEL J . Am. Chem. Soc.
and D. R. KEARNS.
97,462(1975).

2. J. A. BELLand J. D. MACGILLVRAY. J. Chem. Ed. 51,

677 (1974).
3. E.J . COREYand W. C. TAYLOR. J. Am. Chem. Soc.
86,3881(1964).
4. J. R. S C H E F F E R ~M.
I I ~D. OUCHI.Tetrahedron Lett.
223 (1970).
5. H. H. WASSERMAN, J . R. SCHEFFER,and J. L.
COOPER.J. Am. Chem. Soc. W,4991 (1972).
6. F. NAHAVANDI, F. RAZMARA, and M. P. STEVENS.
Tetrahedron Lett. 301 (1973).
7. W. R. ADAMS.In Oxidation. Vol. 2. Edited by R. L.
Augustine and D. J. Trecker. Marcel Dekker Inc.,
New York. 1971.
8. J. A. HOWARDand K. U. INGOLD.Can. J. Chem. 47,
When photooxidation was performed in CCl, or 3809 (1969).
when 1, prepared in benzene, was dissolved @ 9. J. E. BENNETT,J. A. EYRE,and R. SUMMERS.J .
Chem. Soc. Perkin 11,797(1974).
CCI,, ODB was produced quantitatively. The 10. A. LE BERREand R. RATSIMBAZAFY. Bull. Chem.
loss of an oxygen atom from 1 is not easily ex- Soc. Fr. 229 (1963).
plained. However, if 1 is considered to be an 11. J.A. HOWARD. Adv.FreeRadicalChem.4,49(1972).
ozonide it may exist as the zwitterion 3 which 12. F. R. MAYO.Acc.Chem.Res. 1, 193(1968).
13. CH. DUFRAISSE and S. ECARY.C.R. Acad. Sci. 223,
would be readily hydrolyzed to ODB, e.g., 735 (1946).
 This article has been cited by:

1. Marta Martínez-Alonso, Natalia Busto, Larry Danilo Aguirre, Leticia Berlanga, M. Carmen Carrión, José V. Cuevas, Ana M.
Rodríguez, Arancha Carbayo, Blanca R. Manzano, Enrique Ortí, Félix A. Jalón, Begoña García, Gustavo Espino. 2018. Strong
Influence of the Ancillary Ligand over the Photodynamic Anticancer Properties of Neutral Biscyclometalated Ir III Complexes
Bearing 2-Benzoazole-Phenolates. Chemistry - A European Journal 24:66, 17523-17537. [Crossref]
2. Binbin Ding, Shuai Shao, Chang Yu, Bo Teng, Meifang Wang, Ziyong Cheng, Ka-Leung Wong, Ping'an Ma, Jun Lin.
2018. Large-Pore Mesoporous-Silica-Coated Upconversion Nanoparticles as Multifunctional Immunoadjuvants with Ultrahigh
Photosensitizer and Antigen Loading Efficiency for Improved Cancer Photodynamic Immunotherapy. Advanced Materials 11,
1802479. [Crossref]
3. Yosuke Hisamatsu, Naoki Umezawa, Hirokazu Yagi, Koichi Kato, Tsunehiko Higuchi. 2018. Design and synthesis of a 4-
aminoquinoline-based molecular tweezer that recognizes protoporphyrin IX and iron( iii ) protoporphyrin IX and its application
as a supramolecular photosensitizer. Chemical Science 9:38, 7455-7467. [Crossref]
Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

4. Paul I. Dron, Josef Michl, Justin C. Johnson. 2017. Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-
Substituted 1,3-Diphenylisobenzofurans. The Journal of Physical Chemistry A 121:45, 8596-8603. [Crossref]
5. Justin C. Johnson, Josef Michl. 2017. 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission. Topics in Current
Chemistry 375:5. . [Crossref]
6. Krzysztof Żamojć, Magdalena Zdrowowicz, Paweł Błażej Rudnicki-Velasquez, Karol Krzymiński, Bartłomiej Zaborowski, Paweł
Niedziałkowski, Dagmara Jacewicz, Lech Chmurzyński. 2017. The development of 1,3-diphenylisobenzofuran as a highly selective
probe for the detection and quantitative determination of hydrogen peroxide. Free Radical Research 51:1, 38-46. [Crossref]
7. 2015. Inorganic Chemistry 54:11, 5342-5357. [Crossref]
8. Joel N. Schrauben, Yixin Zhao, Candy Mercado, Paul I. Dron, Joseph L. Ryerson, Josef Michl, Kai Zhu, Justin C. Johnson. 2015.
Photocurrent Enhanced by Singlet Fission in a Dye-Sensitized Solar Cell. ACS Applied Materials & Interfaces 7:4, 2286-2293.
For personal use only.

[Crossref]
9. Akin Akdag, Abdul Wahab, Pavel Beran, Lubomír Rulíšek, Paul I. Dron, Jiří Ludvík, Josef Michl. 2015. Covalent Dimers of
1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry. The Journal of Organic Chemistry 80:1, 80-89.
[Crossref]
10. 2015. Inorganic Chemistry 54:11. . [Crossref]
11. Joseph L. Ryerson, Joel N. Schrauben, Andrew J. Ferguson, Subash Chandra Sahoo, Panče Naumov, Zdenĕk Havlas, Josef
Michl, Arthur J. Nozik, Justin C. Johnson. 2014. Two Thin Film Polymorphs of the Singlet Fission Compound 1,3-
Diphenylisobenzofuran. The Journal of Physical Chemistry C 118:23, 12121-12132. [Crossref]
12. Akihiro Nakagawa, Yosuke Hisamatsu, Shinsuke Moromizato, Masahiro Kohno, Shin Aoki. 2013. Synthesis and Photochemical
Properties of pH Responsive Tris-Cyclometalated Iridium(III) Complexes That Contain a Pyridine Ring on the 2-Phenylpyridine
Ligand. Inorganic Chemistry 131217101323009. [Crossref]
13. Marcin Wierzchowski, Lukasz Sobotta, Paulina Skupin-Mrugalska, Justyna Kruk, Weronika Jusiak, Michael Yee, Krystyna
Konopka, Nejat Düzgüneş, Ewa Tykarska, Maria Gdaniec, Jadwiga Mielcarek, Tomasz Goslinski. 2013. Phthalocyanines
functionalized with 2-methyl-5-nitro-1H-imidazolylethoxy and 1,4,7-trioxanonyl moieties and the effect of metronidazole
substitution on photocytotoxicity. Journal of Inorganic Biochemistry 127, 62-72. [Crossref]
14. Lukasz Sobotta, Piotr Fita, Wojciech Szczolko, Maciej Wrotynski, Marcin Wierzchowski, Tomasz Goslinski, Jadwiga Mielcarek.
2013. Functional singlet oxygen generators based on porphyrazines with peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino
groups. Journal of Photochemistry and Photobiology A: Chemistry 269, 9-16. [Crossref]
15. Ethel J. Ngen, Lixin Xiao, Pallavi Rajaputra, Xingzhong Yan, Youngjae You. 2013. Enhanced Singlet Oxygen Generation from a
Porphyrin-Rhodamine B Dyad by Two-Photon Excitation through Resonance Energy Transfer. Photochemistry and Photobiology
89:4, 841-848. [Crossref]
16. Adriel M. Lima, Carine Dal Pizzol, Fabíola B. Filippin Monteiro, Tânia B. Creczynski-Pasa, Gislaine P. Andrade, Anderson O.
Ribeiro, Janice R. Perussi. 2013. Hypericin encapsulated in solid lipid nanoparticles: phototoxicity and photodynamic efficiency.
Journal of Photochemistry and Photobiology B: Biology . [Crossref]
17. A. Sivéry, F. Anquez, C. Pierlot, J.M. Aubry, E. Courtade. 2013. Singlet oxygen () generation upon 1270nm laser irradiation of
ground state oxygen () dissolved in organic solvents: Simultaneous and independent determination of production rate and reactivity
with chemical traps. Chemical Physics Letters 555, 252-257. [Crossref]
 18. Shinsuke Moromizato, Yosuke Hisamatsu, Toshihiro Suzuki, Yasuki Matsuo, Ryo Abe, Shin Aoki. 2012. Design and Synthesis
of a Luminescent Cyclometalated Iridium(III) Complex Having N , N -Diethylamino Group that Stains Acidic Intracellular
Organelles and Induces Cell Death by Photoirradiation. Inorganic Chemistry 51:23, 12697-12706. [Crossref]
19. Jérôme Jacq, Svetlana Tsekhanovich, Maylis Orio, Cathy Einhorn, Jacques Einhorn, Bernard Bessières, Jérôme Chauvin, Damien
Jouvenot, Frédérique Loiseau. 2012. Structure and Dynamics of the Excited States of 1,3-Diarylisobenzofurans: An Experimental
and Theoretical Study. Photochemistry and Photobiology 88:3, 633-638. [Crossref]
20. Haluk Dinçalp, Şevki Kızılok, Özgül Haklı Birel, Sıddık İçli. 2012. Synthesis and G-quadruplex binding study of a novel full
visible absorbing perylene diimide dye. Journal of Photochemistry and Photobiology A: Chemistry 235, 40-48. [Crossref]
21. Wojciech Szczolko, Lukasz Sobotta, Piotr Fita, Tomasz Koczorowski, Michal Mikus, Maria Gdaniec, Aleksandra Orzechowska,
Kvetoslava Burda, Stanislaw Sobiak, Marcin Wierzchowski, Jadwiga Mielcarek, Ewa Tykarska, Tomasz Goslinski. 2012. Synthesis,
characteristics and photochemical studies of novel porphyrazines possessing peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino
groups. Tetrahedron Letters 53:16, 2040-2044. [Crossref]
22. Xian-Fu Zhang, Xiaoli Li. 2011. The photostability and fluorescence properties of diphenylisobenzofuran. Journal of Luminescence
Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

131:11, 2263-2266. [Crossref]

23. Ling Xiao, Luo Gu, Stephen B. Howell, Michael J. Sailor. 2011. Porous Silicon Nanoparticle Photosensitizers for Singlet Oxygen
and Their Phototoxicity against Cancer Cells. ACS Nano 5:5, 3651-3659. [Crossref]
24. Keisuke Nakamura, Kirika Ishiyama, Hiroyo Ikai, Taro Kanno, Keiichi Sasaki, Yoshimi Niwano, Masahiro Kohno. 2011.
Reevaluation of analytical methods for photogenerated singlet oxygen. Journal of Clinical Biochemistry and Nutrition 49:2, 87-95.
[Crossref]
25. Peter R. Ogilby. 2010. Singlet oxygen: there is indeed something new under the sun. Chemical Society Reviews 39:8, 3181.
[Crossref]
26. Michael Höfer, Norbert Moszner, Robert Liska. 2008. Oxygen scavengers and sensitizers for reduced oxygen inhibition in radical
photopolymerization. Journal of Polymer Science Part A: Polymer Chemistry 46:20, 6916-6927. [Crossref]
For personal use only.

27. Hiroaki Isago, Kyoko Miura, Masatoshi Kanesato. 2008. Unexpected photo-initiated oxidation of antimony in (tetra-tert-
butyl)phthalocyaninatoantimony(III) complex in the presence of singlet oxygen acceptors. Journal of Photochemistry and
Photobiology A: Chemistry 197:2-3, 313-320. [Crossref]
28. WOLFGANG SPILLER, HOLGER KLIESCH, DIETER WÖHRLE, STEFFEN HACKBARTH, BEATE RÖDER,
GüNTER SCHNURPFEIL. 1998. Singlet Oxygen Quantum Yields of Different Photosensitizers in Polar Solvents and Micellar
Solutions. Journal of Porphyrins and Phthalocyanines (JPP) 02:02, 145-158. [Crossref]
29. F. Amat-Guerri, E. Lempe, E.A. Lissi, F.J. Rodriguez, F.R. Trull. 1996. Water-soluble 1,3-diphenylisobenzofuran derivatives.
Synthesis and evaluation as singlet molecular oxygen acceptors for biological systems. Journal of Photochemistry and Photobiology
A: Chemistry 93:1, 49-56. [Crossref]
30. GERALD SCOTT. INITIATORS, PROOXIDANTS AND SENSITISERS 83-119. [Crossref]
31. Alexander P. Darmanyan, Galina Móger. 1984. Mechanism of singlet oxygen interaction with spin trap α-phenyl-N-tert-
butylnitrone. Journal of Photochemistry 26:4, 269-274. [Crossref]
32. Paul H. Siedlik, Lawrence J. Marnett. [54] Oxidizing radical generation by prostaglandin H synthase 412-416. [Crossref]
33. Lawrence J. Marnett. Hydroperoxide-Dependent Oxidations during Prostaglandin Biosynthesis 63-94. [Crossref]
34. Jean-Paul Chauvet, Françoise Villain, Roger Viovy. 1981. PHOTOOXIDATION OF CHLOROPHYLL AND PHEOPHYTIN.
QUENCHING OF SINGLET OXYGEN AND INFLUENCE OF THE MICELLAR STRUCTURE. Photochemistry and
Photobiology 34:5, 557-565. [Crossref]
35. Lawrence J. Marnett. 1981. Polycyclic aromatic hydrocarbon oxidation during prostaglandin biosynthesis. Life Sciences 29:6,
531-546. [Crossref]
36. Willy Friedrichsen. Benzo[c]furans 135-241. [Crossref]
37. D. Lala, J.F. Rabek, B. Ranby. 1980. The effect of 1,3-diphenylisobenzofuran on the photo-oxidative degradation of cis-1,4-
polybutadiene. European Polymer Journal 16:8, 735-744. [Crossref]
38. John PIATT, Peter J. O'BRIEN. 1979. Singlet Oxygen Formation by a Peroxidase, H2O2 and Halide System. European Journal
of Biochemistry 93:2, 323-332. [Crossref]
39. Christopher S. Foote. DETECTION OF SINGLET OXYGEN IN COMPLEX SYSTEMS: A CRITIQUE 603-626. [Crossref]
40. Takashi Ito. 1978. CELLULAR AND SUBCELLULAR MECHANISMS OF PHOTODYNAMIC ACTION: THE O 2
HYPOTHESIS AS A DRIVING FORCE IN RECENT RESEARCH. Photochemistry and Photobiology 28:4-5, 493-506.
[Crossref]
 41. Leland L. Smith, Jonathan P. Stroud. 1978. STEROL METABOLISM. XLII. ON THE INTERCEPTION OF SINGLET
MOLECULAR OXYGEN BY STEROLS. Photochemistry and Photobiology 28:4-5, 479-485. [Crossref]
42. Ajit Singh, Neil R. McIntyre, Grant W. Koroll. 1978. PHOTOCHEMICAL FORMATION OF METASTABLE SPECIES
FROM 1,3-DIPHENYLISOBENZOFURAN. Photochemistry and Photobiology 28:4-5, 595-601. [Crossref]
43. Salvatore Cannistraro, Giulio Jori, Albert Vorst. 1978. PHOTOSENSITIZATION OF AMINO ACIDS BY DI-CYAN-HEMIN:
KINETIC AND EPR STUDIES. Photochemistry and Photobiology 27:5, 517-521. [Crossref]
44. Fred J. Hawco, Cindy R. O'Brien, Peter J. O'Brien. 1977. Singlet oxygen formation during hemoprotein catalyzed lipid peroxide
decomposition. Biochemical and Biophysical Research Communications 76:2, 354-361. [Crossref]
45. Ionel Rosenthal. 1976. RECENT DEVELOPMENTS IN SINGLET MOLECULAR OXYGEN CHEMISTRY. Photochemistry
and Photobiology 24:6, 641-645. [Crossref]
46. JAMES A. HOWARD, G. DAVID MENDENHALL. 1975. ChemInform Abstract: AUTOXIDATION AND
PHOTOOXIDATION OF 1,3-DIPHENYLISOBENZOFURAN. A KINETIC AND PRODUCT STUDY. Chemischer
Can. J. Chem. Downloaded from www.nrcresearchpress.com by 92.238.79.143 on 12/06/18

Informationsdienst 6:44, no-no. [Crossref]

For personal use only.