Studies on the origin of dihydrofurans from. alpha.-diazocarbonyl compounds. Concerted 1, 3-dipolar cycloaddition vs. nonsynchronous coupling in the copper chelate …

ME Alonso, A Morales, AW Chitty

Index: Alonso, Miquel E.; Morales, Angelina; Chitty, A. Wladimir Journal of Organic Chemistry, 1982 , vol. 47, # 19 p. 3747 - 3754

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Citation Number: 53

Abstract

The copper chelate catalyzed thermolysis of alkyl 2-diazo-3-oxobutyrate (1) and of 3-diazo- 2, 4-pentanedione (2) in the presence of several vinyl ethers to give 4-(alkoxycarbonyl)-and 4-acyl-2, 3-dihydrofurans is used to probe the mechanism of this transformation in terms of the concerted 1, 3-dipolar cycloaddition of the metaloxocarbene complex vs. the initial formation of the cyclopropane followed by 1, 3 sigmatropic rearrangement to the ...