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Photochemistry of alkenyl‐ and acetal‐substituted pyridines
Author(s) -
Fleming Steven A.,
Bachelder Vance D.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280849
Subject(s) - chemistry , acetal , alkene , acetonitrile , propionate , pyridine , photochemistry , organic chemistry , medicinal chemistry , catalysis
Ethyl 3‐(2‐pyridyl)propionate formation results from irradiation of 3‐(2‐pyridyl)propanal diethylacetal in acetonitrile. This photoreaction is unique to the heteroaromatic pyridine and only occurs in acetonitrile. A minor product, 1‐aza‐2‐methyl‐3‐(2‐ethanal diethylacetal)‐4‐ethoxycycloocta‐1,3,5,7‐tetraene, is also obtained. The irradiation of 2‐methyl‐6‐(2‐pyridyl)‐2‐pentene in the presence of various sensitizers results in addition to the alkene side‐chain to produce oxetanes.