Journal of the American Chemical Society

Intramolecular generation of oxonium ylides from functionalized arylcarbenes

W Kirmse, K Kund

Index: Kirmse, Wolfgang; Kund, Klaus Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1465 - 1473

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Citation Number: 29

Abstract

Abstract: Arylcarbenes carrying alkoxyalkyl groups in the ortho position have been generated by flash pyrolysis and photolysis of appropriate tosylhydrazone sodium salts. In the gas phase and in aprotic solvents, interaction of the carbenes with the lone electron pairs of oxygen competes efficiently with insertion into CH bonds. Both five-and six- membered cyclic oxonium ylides have been generated. The ylides 23, 37, 61b, and 74 ...