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Rh(II)-Catalysed reactions of 2H-azirines with ethyl 2-acyl-2-diazoacetates. Synthesis of novel photochromic oxazines

✍ Scribed by Vsevolod A. Khlebnikov; Mikhail S. Novikov; Alexander F. Khlebnikov; Nikolai V. Rostovskii

Book ID: 104096948
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 287 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.09.033

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✦ Synopsis

Photochromic non-fused 2H-1,4-oxazines are synthesised by a Rh 2 (OAc) 4 -catalysed reaction of 2H-azirines with ethyl 2-acyl-2-diazoacetates. The reaction proceeds via the formation of an azirinium ylide which undergoes ring-opening to a 2-azadiene followed by 1,6-electrocyclisation.

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