Reaction of 3-aroylaziridines with diphenylcyclopropenone. 1,3-Dipole cascade from azomethine ylide to carbonyl ylide

Matsumoto, Kiyoshi; Ikemi, Yukio; Toda, Mitsuo; Kakehi, Akikazu; Uchida, Takane; Lown, J. W.

doi:10.1016/0040-4039(95)00436-g

Cited by 7 publications

(2 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A possible reaction pathway is illustrated in eq 201. The reported examples include the reactions of cyclopropenones with sulfonium ylides 369 , 370 , , and 371 (X = S), selenonium ylides 371 (X = Se) 328 and 372 , and ammonium ylides 373 , , 374 , and 375 . Diphenylcyclopropenethione is also reported to undergo similar reactions with ylides 369 , 376 , , 377 , , and 378 …”

Section: Reaction With Nucleophiles1 Ring Expansionmentioning

confidence: 99%

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

2003

View full text Add to dashboard Cite

Section: Reaction With Nucleophiles1 Ring Expansionmentioning

confidence: 99%

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

2003

View full text Add to dashboard Cite

“…As outlined in Scheme , there are several different synthetic strategies for the generation of N-protonated azomethine ylides ( 289 ) and their N-alkylated cousins ( 290 ) including (1) ring-opening reactions, (2) deprotonation, (3) 1,2-prototropic rearrangement, (4) decarboxylation, (5) disilylation/destannylation, and (6) via carbenes and carbenoids. The most classical method involves the thermal (or photochemical) retro -pericyclic ring opening of aziridines ( 291 ). − The mechanism of this ring-opening process and the ensuing 1,3-dipolar cycloaddtions have been investigated thoroughly. − More recent innovations include the use of Lewis acids to mediate the ring-opening of aziridines to azomethine ylides at lower temperatures. − Dihydrooxazoles ( 292 , X = O), ,− dihydrothiazoles ( 292 , X = S), and related heterocycles ,, also can produce N -alkyl azomethine ylide dipoles via ring-opening processes.…”

Section: Azomethine Ylidesmentioning

confidence: 99%

2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides

et al. 2018

View full text Add to dashboard Cite

This review covers the use of 2-azaallyl anions, 2-azaallyl cations, and 2-azaallyl radicals in organic synthesis up through June 2018. Particular attention is paid to both foundational studies and recent advances over the past decade involving semistabilized and nonstabilized 2-azaallyl anions as key intermediates in various carbon–carbon and carbon–heteroatom bond-forming processes. Both transition-metal-catalyzed and transition-metal-free transformations are covered. Azomethine ylides, which have received significant attention elsewhere, are discussed briefly with the primary focus on critical comparisons with 2-azaallyl anions in regard to generation and use.

show abstract