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Homoconjugated ketones with extended unsaturation: Wavelength‐selective, regioselective, diastereoselective, and enantiospecific photochemical transformations of methyl 7‐oxospiro[5.5]undeca‐1,3‐and ‐2,4,‐diene‐2‐carboxylate
Author(s) -
Oren Jakob,
Vardi Michaela,
Viskin Rossana,
Abramson Sarah,
Fuchs Benzion
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760305
Subject(s) - chemistry , regioselectivity , degree of unsaturation , diene , selectivity , stereochemistry , molecule , photochemistry , organic chemistry , catalysis , natural rubber
The title molecules were shown to photorearrange with remarkable selectivity. Wavelength variation steers the rearrangement modes, of which the [1,2]‐acyl shift was found to be largely regioselective, diastereoselective, and enantiospecific. Chemical intercorrelation of products and mechanistic studies were carried out all along. The potential significance of these photochemical processes in selective synthetic schemes is discussed.