Stereochemical studies. Part 31. Ring closure reaction of cis- and trans-2-(bromomethyl)cycloalkylamines

György Göndös, Kornélia L. Láng, Andrea Szeghy, G. Dombi, G. Bernáth

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Abstract

Cyclization of the cis- and trans-2-(bromomethyl)cycloalkylamines (7)-(12) to the fused-ring azetidines (13)-(17) was investigated. The first-order rate constants for azetidine formation as a function of the ring size are in the order: cycloheptane > cyclopentane > cyclohexane for the cis-isomers; and cycloheptane > cyclohexane for the trans-isomers. Azetidine formation could not be induced from trans-2-(bromomethyl)cyclopentylamine (8). A plot of the E6 values for the reactions as a function of ΔS‡, shows an isokinetic correlation, with the exception of the point for trans-2-(bromomethyl)cyclohexylamine (10), where the main reaction is elimination.

Original languageEnglish
Pages (from-to)1770-1773
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1979

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Cycloheptanes
Isomers
Azetidines
Cyclohexylamines
Cyclopentanes
Cyclization
Rate constants
Cyclohexane
azetidine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereochemical studies. Part 31. Ring closure reaction of cis- and trans-2-(bromomethyl)cycloalkylamines. / Göndös, György; Láng, Kornélia L.; Szeghy, Andrea; Dombi, G.; Bernáth, G.

In: Journal of the Chemical Society, Perkin Transactions 1, 1979, p. 1770-1773.

Research output: Contribution to journalArticle

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AU - Dombi, G.

AU - Bernáth, G.

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