An Adduct (1:2) from Diphenylcyclopropenone Oxime and Phenyl Isocyanate

Abstract

Diphenylcyclopropenone oxime combined with phenyl isocyanate to give 1,2,7-triphenyl-4-[(phenylamino)carbonyl]-5-oxa-4,7-diazaspiro-[2.4]hept-1-en-6-one.

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

“…265 When diphenylcyclopropenone oxime was treated with phenyl isocyanate, however, a 1:2 adduct 282 was obtained. 266 Reaction with halogenating reagents SOCl 2 , SOBr 2 , and PCl 5 resulted in ring opening to give 283. 265…”

“…Reaction of diphenylcyclopropenone oxime with isocyanates RNCO (R = acetyl, tosyl), acid anhydrides (RCO) 2 O (R = alkyl, aryl), and 2,4-(NO 2 )C 6 H 3 F in the presence of Et 3 N have been reported to give O -substituted oximes 281a , 281b , and 281c , respectively (eq 165) . When diphenylcyclopropenone oxime was treated with phenyl isocyanate, however, a 1:2 adduct 282 was obtained . Reaction with halogenating reagents SOCl 2 , SOBr 2 , and PCl 5 resulted in ring opening to give 283 …”

Cyclopropenone AcetalsSynthesis and Reactions

“…The reaction of the cyclopropenone oxime 133 with an isocyanate gives an aminal derivative 134 (Scheme ) . The reaction of 133 with an isocyanate was first reported in 1987. , However, the structure of the product was erroneously identified initially and later correctly identified to be 134 from X-ray crystallographic analysis . The cycloadduct 134 is formed by the [3 + 2] cycloaddition of the nitrone intermediate with isocyanate.…”

“…128,129 However, the structure of the product was erroneously identified initially and later correctly identified to be 134 from X-ray crystallographic analysis. 127 The cycloadduct 134 is formed by the [3 + 2] cycloaddition of the nitrone intermediate with isocyanate.…”

Alkyne and Reversible Nitrile Activation: N,N′-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines

“…The isolated product was identified as cyclopropene 2a (Figure bottom), in part on the basis of the appearance of signals associated with a strained olefin observed at 7.23 (2H) and 117.9 ppm (CDCl 3 ) in the compound’s 1 H and 13 C NMR spectra, respectively. The structure of 2a , which constitutes a rare example of a diamidocyclopropene, was unambiguously elucidated by single-crystal X-ray diffraction (XRD) analysis (Figure ).…”