Accession Number : AD0640715

Title :   STUDIES IN THE CYCLOBUTANE SERIES.

Descriptive Note : Final rept., 2 Oct 63-1 Sep 66,

Corporate Author : MIAMI UNIV FLA DEPT OF PEDIATRICS

Personal Author(s) : Lillien,Irving

Report Date : 01 SEP 1966

Pagination or Media Count : 13

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)

Descriptors :   (*CYCLOBUTANES, *STEREOCHEMISTRY), SYNTHESIS(CHEMISTRY), MOLECULAR ISOMERISM, ESTERS, CHEMICAL EQUILIBRIUM, AMINES, ALCOHOLS, NUCLEAR MAGNETIC RESONANCE, MOLECULAR STRUCTURE

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE