Diverse photochemistry of sterically congested. alpha.-arylacetophenones: ground-state conformational control of reactivity

PJ Wagner, T Hasegawa, B Zhou…

Index: Wagner, Peter J.; Zhou, Boli; Hasegawa, Tadashi; Ward, Donald L. Journal of the American Chemical Society, 1991 , vol. 113, # 25 p. 9640 - 9654

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Citation Number: 33

Abstract

Abstract: The effects of a and ortho substituents on the photoreactivity of various a-(0-tolyl)- and a-mesitylacetophenones have been measured. In general, both types of substitution lower the efficiency of cyclization to 2-indanol derivatives in solution. I, 3-Rearrangement of an a-mesityl group to form enol ethers and a-cleavage to radicals compete to various degrees, in some cases becoming dominant. Quenching studies in solution show that all ...

 Related Synthetic Route
Mesitylacetonitrile Structure

34688-71-6

Mesitylacetonitrile

~%

1-phenyl-2-(2,4,6-trimethylphenyl)pentan-1-one Structure

112247-46-8

1-phenyl-2-(2,4...

2,4,6-Trimethyl benzyl chloride Structure

1585-16-6

2,4,6-Trimethyl...

~%

1-phenyl-2-(2,4,6-trimethylphenyl)pentan-1-one Structure

112247-46-8

1-phenyl-2-(2,4...

Benzeneacetic acid,2,4,6-trimethyl-a-phenyl- Structure

3901-04-0

Benzeneacetic a...

~%

Mesitaldehyde Structure

487-68-3

Mesitaldehyde

N/A Structure

97799-60-5

N/A

~%

Mesitaldehyde Structure

487-68-3

Mesitaldehyde

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

1889-72-1

2-phenyl-1-(2,4...

~%

Mesitaldehyde Structure

487-68-3

Mesitaldehyde

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

77787-77-0

Ethanone, 2-phe...

~%

Mesitaldehyde Structure

487-68-3

Mesitaldehyde

α-mesityl-2,4,6-trimethylacetophenone Structure

5796-78-1

α-mesityl-2,4,6...

~%

Mesitaldehyde Structure

487-68-3

Mesitaldehyde

Phenylacetyl chloride Structure

103-80-0

Phenylacetyl ch...

Mesitylene Structure

108-67-8

Mesitylene

~%

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

1889-72-1

2-phenyl-1-(2,4...

Benzeneacetic acid,2,4,6-trimethyl-a-phenyl- Structure

3901-04-0

Benzeneacetic a...

~%

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

77787-77-0

Ethanone, 2-phe...

Mesitylene Structure

108-67-8

Mesitylene

~%

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

77787-77-0

Ethanone, 2-phe...

N/A Structure

97799-60-5

N/A

Mesitylene Structure

108-67-8

Mesitylene

~%

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

77787-77-0

Ethanone, 2-phe...

α-(o-tolyl)isobutyrophenone Structure

136667-03-3

α-(o-tolyl)isob...

~%

o-Isopropenyltoluene Structure

7399-49-7

o-Isopropenyltoluene

o-Cymene Structure

527-84-4

o-Cymene

Benzaldehyde Structure

100-52-7

Benzaldehyde

Mesitylacetonitrile Structure

34688-71-6

Mesitylacetonitrile

~%

1-phenyl-2-(2,4,6-trimethylphenyl)propan-1-one Structure

84839-90-7

1-phenyl-2-(2,4...

2,4,6-Trimethyl benzyl chloride Structure

1585-16-6

2,4,6-Trimethyl...

~%

1-phenyl-2-(2,4,6-trimethylphenyl)propan-1-one Structure

84839-90-7

1-phenyl-2-(2,4...

α-mesityl-o-methylacetophenone Structure

136667-06-6

α-mesityl-o-met...

~%

1,3,5-trimethyl-2-[2-(2,4,6-trimethylphenyl)ethyl]benzene Structure

4674-23-1

1,3,5-trimethyl...

N/A Structure

136667-29-3

N/A

2-Methylbenzaldehyde Structure

529-20-4

2-Methylbenzaldehyde


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