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 journalArticle

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

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Phenothiazines
Hydrolysis
Ethers
Isomers
Kinetics
phenothiazine
phenylacetylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

10-Alkenylphenothiazines. 2. Synthesis and mechanism of acidic hydrolysis of cis- and trans-10-2-phenylvinyl)phenothiazines. / Anfinogenov, V. A.; Napilkova, O. A.; Sirotkina, E. E.; Filimonov, V. D.; Khlebnikov, Andrey Ivanovich.

In: Chemistry of Heterocyclic Compounds, Vol. 22, No. 10, 10.1986, p. 1152-1157.

Research output: Contribution to journalArticle

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