STUDIES IN THE CYCLOBUTANE SERIES.
Abstract
The primary accomplishments included the synthesis and study of derivatives of the 3-isopropylcyclobutane system, which provided successful ingress to means for defining conformational consequences of nonplanarity. Cis and trans 3-isopropylcyclobutanecarboxylate esters were equilibrated: cis and trans 3-isopropylcyclobutylamines and cis and trans 3-isopropylcyclobutanols were synthesized and configurational assignments made by reference to equilibrated ester. NMR spectra of the above series of compounds, and the equilibration data, strongly support the conclusion that the isopropyl group is effective as a 'holding' group in this system, the alcohols and amines appear to be conformationally homogeneous. Deamination of the cis and trans amines produce a mixture of the same five products but in significantly different ratios. Thus, there is little or no likelihood of a common intermediate, classical or non-classical, and results are interpreted in terms of concertion involving the conformational distinction between equatorial and axial amino groups. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Sep 01, 1966
- Accession Number
- AD0640715
Entities
People
- Irving Lillien
Organizations
- University of Miami