Photocyclization of. alpha.-(o-tolyl) acetophenones: triplet and 1, 5-biradical reactivity

PJ Wagner, MA Meador, B Zhou…

Index: Wagner, Peter J.; Meador, Michael A.; Zhou, Boli; Park, Bong-Ser Journal of the American Chemical Society, 1991 , vol. 113, # 25 p. 9630 - 9639

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Citation Number: 46

Abstract

Abstract: Several ring-substituted a-(0-toly1) acetophenones undergo photocyclization to 2- indanol derivatives in high quantum efficiency in solution and in high chemical yield as solids. The mechanism for reaction involves triplet state &hydrogen atom abstraction that generates 1, 5-biradicals. Quenching studies indicate that the n, a* excited triplets of these ketones react, with rate constants> IO8 sl. Variations in triplet reactivity are ascribed to ...

 Related Synthetic Route
N/A Structure

90432-29-4

N/A

~%

3,3-dimethyl-2-phenyl-5,7-di(propan-2-yl)-1H-inden-2-ol Structure

90432-31-8

3,3-dimethyl-2-...

N/A Structure

90432-30-7

N/A

N/A Structure

90460-01-8

N/A

1,3,5-Triisopropylbenzene Structure

717-74-8

1,3,5-Triisopro...

~%

2-(CHLOROMETHYL)-1,3,5-TRIISOPROPYLBENZENE Structure

38580-86-8

2-(CHLOROMETHYL...

2,4,6-TRIISOPROPYLBENZOIC ACID Structure

49623-71-4

2,4,6-TRIISOPRO...

~%

2-(CHLOROMETHYL)-1,3,5-TRIISOPROPYLBENZENE Structure

38580-86-8

2-(CHLOROMETHYL...

(2,4,6-TRIISOPROPYLPHENYL)METHANOL Structure

4276-88-4

(2,4,6-TRIISOPR...

~%

2-(CHLOROMETHYL)-1,3,5-TRIISOPROPYLBENZENE Structure

38580-86-8

2-(CHLOROMETHYL...

α-Bromo-o-xylene Structure

89-92-9

α-Bromo-o-xylene

~%

1-(2-methylphenyl)propan-2-one Structure

51052-00-7

1-(2-methylphen...

1,3,5-Triisopropylbenzene Structure

717-74-8

1,3,5-Triisopro...

Carbon dioxide Structure

124-38-9

Carbon dioxide

~%

2,4,6-TRIISOPROPYLBENZOIC ACID Structure

49623-71-4

2,4,6-TRIISOPRO...

1,4-Diisopropylbenzene Structure

100-18-5

1,4-Diisopropyl...

~%

2,5-di(propan-2-yl)benzoic acid Structure

57988-33-7

2,5-di(propan-2...

Carbon dioxide Structure

124-38-9

Carbon dioxide

2-bromo-1,4-di(propan-2-yl)benzene Structure

42196-29-2

2-bromo-1,4-di(...

~%

2,5-di(propan-2-yl)benzoic acid Structure

57988-33-7

2,5-di(propan-2...

Mesitylacetonitrile Structure

34688-71-6

Mesitylacetonitrile

Phenyllithium Structure

591-51-5

Phenyllithium

~62%

Ethanone,1-phenyl-2-(2,4,6-trimethylphenyl)- Structure

5350-76-5

Ethanone,1-phen...

o-xylyllithium Structure

59305-26-9

o-xylyllithium

benzoic acid Structure

65-85-0

benzoic acid

~35%

2-(2-methylphenyl)-1-phenyl-ethanone Structure

5033-67-0

2-(2-methylphen...

2-Bromoethylbenzene Structure

1973-22-4

2-Bromoethylbenzene

~%

2-(2-ethylphenyl)acetonitrile Structure

74533-20-3

2-(2-ethylpheny...

2-Ethylbenzoic acid Structure

612-19-1

2-Ethylbenzoic acid

~%

2-(2-ethylphenyl)acetonitrile Structure

74533-20-3

2-(2-ethylpheny...

2,5-Dimethylbromobenzene Structure

553-94-6

2,5-Dimethylbro...

~%

2-(2,5-dimethylphenyl)-1-phenylethanone Structure

85995-31-9

2-(2,5-dimethyl...

(2,5-Dimethylphenyl)methanol Structure

53957-33-8

(2,5-Dimethylph...

~%

2-(2,5-dimethylphenyl)-1-phenylethanone Structure

85995-31-9

2-(2,5-dimethyl...

2,5-Dimethylbenzoic acid Structure

610-72-0

2,5-Dimethylben...

~%

2-(2,5-dimethylphenyl)-1-phenylethanone Structure

85995-31-9

2-(2,5-dimethyl...

2,5-Dimethylbenzylchloride Structure

824-45-3

2,5-Dimethylben...

~%

2-(2,5-dimethylphenyl)-1-phenylethanone Structure

85995-31-9

2-(2,5-dimethyl...


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