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[2 + 2]‐Cycloaddition of N,N ‐Dimethyl‐ N (2‐methyl‐1‐propenylidene)ammonium (“Tetramethylketeniminium”) Ion to α,β‐Unsaturated Carbonyl Compounds
Author(s) -
Heine HansGeorg,
Hartmann Willy
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198107821
Subject(s) - cycloaddition , chemistry , ammonium , medicinal chemistry , ion , organic chemistry , catalysis
The title compoud (1) is considerably more reactive than ketenes in [2 + 2]‐cycloadditions and even reacts with α,β‐unsaturated carbonyl compounds due to the presence of extremely low‐lying unoccupied MO's. Mechanisms, which explain the orientation of the subtituents in the cyclobutanones (2) and (3) formed, are discussed.