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2005
Intermediates
O 0190
Reaction of Difluorocarbene with 2H-Azirines: Generation and Transformations
Strained Azomethine Ylides — Aziriniodifluoromethanides. — Reaction of
03- 050 of
monosubstituted azirines with difluorocarbene generates a new type of azomethine
ylides, namely aziriniodifluoromethanides, which can be trapped by cycloaddition with
active dipolarophiles like DMAD or aldehydes. Reaction with DMAD produces azabicyclohexenedicarboxylates (IV) which are stable at low temperatures but undergo
ring expansion during storage at room temperature to give pyridine derivatives (V).
Ylides derived from di- or trisubstituted azirines only undergo isomerization to isocyanates [cf. (XIX) and (XXI)]. — (KHLEBNIKOV*, A. F.; NOVIKOV, M. S.; AMER,
A. A.; Russ. Chem. Bull. 53 (2004) 5, 1092-1101; Inst. Chem., St. Petersburg State
Univ., St. Petersburg 198504, Russia; Eng.) — Mischke
2005
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