Steric factors in the azidolysis-thermolysis of some 5-tosyloxymethylbi- cyclo[2.2.2]oct-2-enes to yield 4-azatetracyclo[4.4.0.02,4.03,8]decanes

Sándor Berényi, Gyöngyi Gulyas, G. Batta, Támas Gunda, Sándor Makleit

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Azidolysis of C-19 diastereoisomer tosylesters of morphine derivatives possessing a bridged ring C has been studied and 4-azatetracyclo[4.4.02,4.03,8]decanes 6b, 6d and 6f were formed via the substitution and subsequent intramolecular cyclization of the (/?)-C-19 tosylesters 4b, 4d and 4f, and primarily the ethylidene derivatives 7a, 7b and 7c were obtained from (S)-C-19 tosylesters 4c, 4e and 4g. According to our experience the course of the reaction depends on the configuration of the C-19 centre of chirality and on the spatial requirement of the substitutent on C-6.

Original languageEnglish
Pages (from-to)1139-1142
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number5
DOIs
Publication statusPublished - 1991

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Morphine Derivatives
Thermolysis
Chirality
Cyclization
Substitution reactions
Derivatives
decane

ASJC Scopus subject areas

  • Chemistry(all)

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Steric factors in the azidolysis-thermolysis of some 5-tosyloxymethylbi- cyclo[2.2.2]oct-2-enes to yield 4-azatetracyclo[4.4.0.02,4.03,8]decanes. / Berényi, Sándor; Gulyas, Gyöngyi; Batta, G.; Gunda, Támas; Makleit, Sándor.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 5, 1991, p. 1139-1142.

Research output: Contribution to journalArticle

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