Determination of the stereochemistry of the monomethylated homologues of 1-chloro- and 1-bromo-1-methylcyclobutane by means of NMR spectroscopy

✍ Scribed by Reinhard Hittich

• Publisher: John Wiley and Sons
• Year: 1982
• Tongue: English
• Weight: 365 KB
• Volume: 18
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1270180409

✦ Synopsis

Abstract

The 300 MHz ^1^H NMR spectra of 1‐chloro‐ and 1‐methylcyclobutane and all monomethylated homologues are reported and analysed with regard to the ring conformations. The results indicate that halogen substituents in methylated halocyclobutanes have a greater preference for the pseudo equatorial position than do methyl groups. The ^13^C NMR spectral data are given, and substituent parameters for halogen substituents and methyl groups are calculated. Of note are the variable γ effects, especially the remarkable difference between the γ‐methyl effects of the stereo‐isomeric 1,3‐substituted cyclobutane compounds.