e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A photo-Favorskii ring contraction reaction: the effect of ring size

…, D Heger, P Klán, M Rubina, RS Givens

Index: Kammath, Viju Balachandran; Solomek, Tomas; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klan, Petr; Rubina, Marina; Givens, Richard S. Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1718 - 1729

Full Text: HTML

Citation Number: 10

Abstract

The effect of ring size on the photo-Favorskii induced ring-contraction reaction of the hydroxybenzocycloalkanonyl acetate and mesylate esters (7a–d, 8a–c) has provided new insight into the mechanism of the rearrangement. By monotonically decreasing the ring size in these cyclic derivatives, the increasing ring strain imposed on the formation of the elusive bicyclic spirocyclopropanone 20 results in a divergence away from rearrangement and ...

5-Hydroxy-1-indanone Structure

5-Hydroxy-1-indanone

~%

2,3-dihydro-1H-indene-1,5-diol Structure

2,3-dihydro-1H-...

5-(benzyloxy)-2,3-dihydro-1-oxo-1H-inden-2-yl acetate Structure

5-(benzyloxy)-2...

~%

2,3-dihydro-1H-indene-1,5-diol Structure

2,3-dihydro-1H-...

N/A Structure

~%

2,3-dihydro-1H-indene-1,5-diol Structure

2,3-dihydro-1H-...

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

5-(BENZYLOXY)-2...

~%

2,3-dihydro-1H-indene-1,5-diol Structure

2,3-dihydro-1H-...

Triphenylphosphine Structure

Triphenylphosphine

~%

5-(3-Methoxyphenyl)pentanoic acid Structure

5-(3-Methoxyphe...

N/A Structure

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

N/A Structure

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-(benzyloxy)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Structure

2-(benzyloxy)-6...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

Triphenylphosphine Structure

Triphenylphosphine

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

(3-Carboxypropyl)(triphenyl)phosphonium bromide Structure

(3-Carboxypropy...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

(Z)/(E)-5-(3-methoxyphenyl)pent-4-enoic acid Structure

(Z)/(E)-5-(3-me...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

5-(3-Methoxyphenyl)pentanoic acid Structure

5-(3-Methoxyphe...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one Structure

2-Methoxy-6,7,8...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6-bromo-6,7,8,9-tetrahydro-2-hydroxybenzo[7]annulen-5-one Structure

6-bromo-6,7,8,9...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6,7,8,9-tetrahydro-2-hydroxy-5-oxo-benzo[7]annulen-6-yl methanesulfonate Structure

6,7,8,9-tetrahy...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

N/A Structure

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6-bromo-6,7,8,9-tetrahydro-2-hydroxybenzo[7]annulen-5-one Structure

6-bromo-6,7,8,9...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6-bromo-6,7,8,9-tetrahydro-2-hydroxybenzo[7]annulen-5-one Structure

6-bromo-6,7,8,9...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6,7,8,9-tetrahydro-2-hydroxy-5-oxo-benzo[7]annulen-6-yl methanesulfonate Structure

6,7,8,9-tetrahy...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

Triphenylphosphine Structure

Triphenylphosphine

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

(3-Carboxypropyl)(triphenyl)phosphonium bromide Structure

(3-Carboxypropy...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

(Z)/(E)-5-(3-methoxyphenyl)pent-4-enoic acid Structure

(Z)/(E)-5-(3-me...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

5-(3-Methoxyphenyl)pentanoic acid Structure

5-(3-Methoxyphe...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one Structure

2-Methoxy-6,7,8...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

2-(benzyloxy)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Structure

2-(benzyloxy)-6...

~%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

N/A Structure

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

Detail

2-(benzyloxy)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Structure

2-(benzyloxy)-6...

~%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

Detail

N/A Structure

~57%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

6,7,8,9-tetrahydro-2-hydroxy-5-oxo-benzo[7]annulen-6-yl methanesulfonate Structure

6,7,8,9-tetrahy...

~76%

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

1-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- Structure

1-NAPHTHALENECA...

N/A Structure

~48%

N/A Structure

1,2,3,4-Tetrahydronaphthalene-1,6-diol Structure

1,2,3,4-Tetrahy...

2-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one Structure

2-hydroxy-6,7,8...

Detail