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Synthesis and Reactions of N-Phthalimido-ketene-S,S-acetals
Doelling, W.,Herrmann, C.,Augustin, M.,Giering, S.
, p. 198 - 207 (2007/10/02)
N-substituted phthalimido derivatives 1a-f react in the presence of bases (NaH, t-BuONa) with carbon disulfide to the N-phthalimido-ketene-S,S-acetals 3, 4, 5 and 6, respectively. 2-Amino-ketene-S,S-acetals 7a-c are formed by reaction of 3a,b or 5a with hydrazine hydrate. 3c produces with phenylhydrazine the pyrazole 8, and with piperidine and pyrrolidine the E/Z mixture of the corresponding ketene-S,N-acetals 9a,b. 1c is transformed into 10a-c (E/Z mixture) by treatment with phenylisothiocyanate under basic condition followed by alkylation.
