Photochemical EZ-isomerization of α,β-unsaturated amides and thioamides in the solid state

Kazushi Kinbara, Kazuhiko Saigo

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The solid-state EZ-isomerizability of α,β-unsaturated amides, which had low isomerizability in the solid state, was greatly improved by modifying their structure; EZ-isomerizability was attained by replacing the carbonyl group of the amides by a thiocarbonyl group as well as replacing the heterochiral N-substituent of the amides by a homochiral one. Crystallographic analyses have revealed that the isomerizability of α,β-unsaturated amides and thioamides in the solid state partially depends on their molecular conformation in crystal. In addition, it was found that the packing coefficient has a correlation with the isomerizability; a smaller value of the packing coefficient caused an increased formation of (Z)-isomers.

Original languageEnglish
Pages (from-to)779-784
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume69
Issue number3
DOIs
Publication statusPublished - 1996 Mar

ASJC Scopus subject areas

  • Chemistry(all)

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