ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The photochemical behaviour of saturated aliphatic (2, 4, and 5) and bicyclic (18 and 19) β-keto sulfoxides has been studied. Photostereomutation of the sulfoxide group was observed on irradiation of 4a, 4b, 18, and 19. Most likely an internal energy transfer from the excited carbonyl to the sulfoxide group is operating on direct irradiation of such compounds.Prolonged photolysis of an aliphatic β-keto sulfoxide, which is nonalkylated a t the α-carbon (2), yielded a product due to preferential (Cα-S)-cleavage (24). Mono- (4) and dialkylated- (5,6, and 8)analogues primarily afforded products due to α-cleavage (26-31 and 32). The carboxylic acid S-methylesters (26-31) were exclusively formed by an intermolecular path. Prolonged irradiation of the bicyclic β-keto sulfoxides 18 and 19 favored the formation of a desulfurized compound 34 due to initial (Cα-S)-cleavage.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19710540761
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