Triplet-sensitized photoisomerization of 1, 4-disubstituted benzonorbornadienes. Intramolecular competition by electronically diverse bridgehead functionality

LA Paquette, A Varadarajan, E Bay

Index: Paquette,L.A.; Varadarajan,A.; Bay,E. Journal of the American Chemical Society, 1984 , vol. 106, p. 6702

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Citation Number: 32

Abstract

Abstract: A general synthetic route to 1-methoxy-4-X-benzonorbornadienes has been devised. Acetophenone-sensitized photoisomerization of six derivatives has been carried out. When X represents groups that are powerfully electron withdrawing, a single reaction channel is followed leading to 23. Only when X= NHCOCH3 or CH3 is leveling encountered. The observed control of regioselectivity points to operation of a direct 1, 2-aryl shift ...

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3-methoxy-1H-indene Structure

27973-23-5

3-methoxy-1H-indene

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Methyl 3-oxo-2,3-dihydro-1H-indene-1-carboxylate Structure

29427-70-1

Methyl 3-oxo-2,...

1-Indanone Structure

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1-Indanone

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Methyl 3-oxo-2,3-dihydro-1H-indene-1-carboxylate Structure

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Trimethyl ortho...

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3-methoxy-1H-indene Structure

27973-23-5

3-methoxy-1H-indene

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124-38-9

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3-methoxy-1H-indene Structure

27973-23-5

3-methoxy-1H-indene

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3-Oxo-1-indanecarboxylic acid Structure

29427-69-8

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3-Oxo-1-indanecarboxylic acid Structure

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1-methoxy-4-(hydroxymethyl)benzonorbornadiene Structure

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

3-methoxy-1H-indene Structure

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3-methoxy-1H-indene

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

3-Oxo-1-indanecarboxylic acid Structure

29427-69-8

3-Oxo-1-indanec...

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

Methyl 3-oxo-2,3-dihydro-1H-indene-1-carboxylate Structure

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

1-Indanone Structure

83-33-0

1-Indanone

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

N/A Structure

91948-52-6

N/A

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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1,4-Methanonaph...

N/A Structure

91948-50-4

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1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

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methyl (3aR,4R,9S,9aS)-9-methoxy-1,3-dioxo-3,3a,9,9a-tetrahydro-4,9-methanonaphtho[2,3-c]furan-4(1H)-carboxylate Structure

91948-51-5

methyl (3aR,4R,...

~%

1,4-Methanonaphthalene-1(4H)-carboxaldehyde, 4-methoxy Structure

91948-69-5

1,4-Methanonaph...


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