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Cycloaddition of Azosulfones and Sulfonylimines
Author(s) -
Effenberger F.,
Maier R.
Publication year - 1966
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.196604162
Subject(s) - library science , stuttgart , chemistry , humanities , computer science , philosophy
Ketene N,N-acetals ( I ) and ketene 0,N-acetals (2) containing hydrogen in the 2-position afford P-substitution products when treated with compounds such as isocyanates and isothiocyanates that contain an electrophilic double bond system[l~zl. However, azosulfones (3) [31 and N-sulfonylimines (7) [41 react with ketene N,N-acetals ( I ) by cycloaddition, affording the hitherto unknown 1,2-dihydro-1,2-diazetes (5) (Table 1) and 1,2-dihydroazetes ( 9 ) (Table 2), respectively. Ketene 0,N-acetals (2) and azosulfones (3), under comparable conditions, also give 1,2-dihydro-1,2-diazetes (5).