10-Alkenylphenothiazines. 2. Synthesis and mechanism of acidic hydrolysis of cis- and trans-10-2-phenylvinyl)phenothiazines

V. A. Anfinogenov, O. A. Napilkova, E. E. Sirotkina, V. D. Filimonov, Andrey Ivanovich Khlebnikov

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The addition of phenothiazine to phenylacetylene in super-base media proceeds regio- and stereoselectively and leads to the predominant formation of cis-10-(2-phenylvinyl)phenothiazine, which is completely converted to its trans-isomer at 200‡C. Kinetic analysis of the acidic hydrolysis of the cis- and transisomers has allowed us to assign to it an ASE2 reaction mechanism, similar to the mechanism of hydrolysis of vinyl alkyl ethers.

Original languageEnglish
Pages (from-to)1152-1157
Number of pages6
JournalChemistry of Heterocyclic Compounds
Volume22
Issue number10
DOIs
Publication statusPublished - Oct 1986

ASJC Scopus subject areas

  • Organic Chemistry

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