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Mesoionic compounds VIII. Synthesis of 3‐phenylsydnonyl substituted alkenes. Some new photochromic sydnones
Author(s) -
Greco Claude V.,
O'Reilly Bernard P.
Publication year - 1972
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.5570090207
Subject(s) - chemistry , photochromism , cyclohexene , mesoionic , wittig reaction , ketone , organic chemistry , catalysis
The reactions of 3‐phenylsydnonyllithium with a variety of ketones to afford tertiary carbinols 4a‐4i and their subsequent dehydration to 4‐(3‐phenylsydnonyl) alkenes 5a‐5i are discussed. Among the alkenes, 2‐[4‐(3‐phenylsydnonyl)]propene ( 5b ) and 1‐[4‐(3‐phenylsydnonyl)]‐1‐cyclohexene ( 5i ) were photochromic. A Wittig reaction between ethyl‐4‐(3‐phenylsydnonyl)‐ketone and methylenetriphenylphosphorane afforded the photochromic 2‐[4‐(3‐phenylsydnon‐yl)]‐1‐butene( 5j ).