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Methyl Shifts in 1,4‐Dipoles from Sulfonyl Isocyanates and Ketene O,N ‐Acetals
Author(s) -
Schaumann Ernst,
Marr Torsten,
Nimmesgern Hildegard,
Sieveking Stefan
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200314
Subject(s) - ketene , chemistry , sulfonyl , scrambling , deuterium , intermolecular force , medicinal chemistry , molecule , stereochemistry , computational chemistry , organic chemistry , alkyl , linguistics , philosophy , physics , quantum mechanics
At low temperature, sulfonyl isocyanates 1 react with ketene O,N ‐acetals 2 to give 1,4‐dipoles 3 . On warming, dipoles 3 rearrange in a formal O → N methyl sift to give malonamides 4 . A crossover experiment starting from 2a and 2b with a deuterated O ‐methyl group gave scrambling of the label and thus confirmed the intermolecular nature of the methyl transfer.