Competitive [4 + 2]-Cycloaddition versus [1,5]-Hydrogen Sigmatropy in a Cycloheptatriene. An Efficient Route to 3-Azatricyclo[5.3.1.04,10]undeca-5,8-diene

Grant R. Krow, Kevin C. Cannon, James T. Carey, Ma Hong, Raghavachari Ramesh, Steven W. Szczepanski

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Thermal rearrangements of N-acyl-7-aminocyclohepta-1,3,5-trienes 7b-e in octane or xylene provide [4 + 2]-cycloaddition products 8b-e and [1,5]-hydrogen sigmatropic rearrangement products 9b-e. The relative rate of formation for 8e/9e is 1.5 in refluxing octane. At a higher reaction temperature in xylene and longer reaction times, 7b afforded a second hydrogen-shift product 10b. No thermal [3,3]-carbon shift products were observed from IV-allyl cycloheptatrienes 9b-e or 10b in octane or xylene. The thermal behavior of 7b-e can be contrasted with that of O-allyl cyclohepta-1,3,5-triene 1.

Original languageEnglish (US)
Pages (from-to)2665-2668
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number12
DOIs
StatePublished - Oct 1 1988

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Competitive [4 + 2]-Cycloaddition versus [1,5]-Hydrogen Sigmatropy in a Cycloheptatriene. An Efficient Route to 3-Azatricyclo[5.3.1.0<sup>4,10</sup>]undeca-5,8-diene'. Together they form a unique fingerprint.

  • Cite this