Influence of 1,2‐Functionalization with CN, CHNR, or CHO on the Stability of the Cyclobutane System

Abstract

Studies on the extent of possible substitution of cyclobutane led to surprising results. (1), R  alkyl, aryl, is known to arise by spontaneous dimerization of acrylonitriles whereas the analogous aldehyde (3) can only be detected by formation of the “Diels-Alder dimer” (4), RCH3 (via methylthioacrolein). (2) was not isolated; its product with iPrNH2 decomposes only at 130°C.