Mesoionic compounds VIII. Synthesis of 3‐phenylsydnonyl substituted alkenes. Some new photochromic sydnones | Zendy

Greco Claude V. | Zendy; O'Reilly Bernard P. | Zendy

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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 ).

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