Indole formation by pyrolysis of β-styrylazides

✍ Scribed by Kazuaki Isomura; Shinjiro Kobayashi; Hiroshi Taniguchi

• Book ID: 104249654
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 199 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99093-8

✦ Synopsis

Cyclization to indole ring from p-styrylnitrene or other intermediates related to it was ambiguous. In case of the deoxygenation of p-nitrostyrene, accompanied with the formation of phenylacetonitrile in low yield, a positive indole test was reported, but not yet specified (1). Recently Boyer and his coworkers found that photolyses of P-styrylazide and p-styrylisocyanate and pyrolysis of the former gave the same nitrile (2). They proposed that P-styrylnitrene might be possible common intermediate for these three reactions. Neither cyclization to indole nor formation of 2-phenyl-2H-azirine, which could be expected from usual decomposition of vinylazides (3), have been confirmed in these reactions of P-styrylnitrene.