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Influence of 1,2‐Functionalization with CN, CHNR, or CHO on the Stability of the Cyclobutane System

1979; Wiley; Volume: 18; Issue: 11 Linguagem: Inglês

10.1002/anie.197908721

1521-3773

Karl‐Dietrich Gundermann, Paul‐Josef Hnida,

Chemical Synthesis and Analysis

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.