The [6+4] photocycloaddition of 3-phenyl-2,2-dimethyl-2H-azirine to fulvenes

✍ Scribed by Albert Padwa; Frederick Nobs

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 212 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)85052-8

✦ Synopsis

1,3-Dipolar cycloadditions of nitrile ylides have been shown to be an astonishingly fruitful synthetic method for the preparation of a wide variety of five-membered heterocyclic rings. 132 These reactions can be considered to be orbital symmetry allowed 4~~ + BITT cycloadditions where the nitrile ylide, with its ally1 anion type MO, functions as a HIT reactant and the dipolarophile as a ~TI reactant.3 Nitrile ylides may also cycloadd to trienes in a symmetry allowed 6~r~ f BITT thermal process.