Organic letters

Dehydrative Fragmentation of 5-Hydroxyalkyl-1 H-tetrazoles: A Mild Route to Alkylidenecarbenes

DJ Wardrop, JP Komenda

Index: Wardrop, Duncan J.; Komenda, John P. Organic Letters, 2012 , vol. 14, # 6 p. 1548 - 1551

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Citation Number: 17

Abstract

The development of a mild, base-free method for the generation of alkylidenecarbenes is reported. Treatment of 5-hydroxyalkyl-1 H-tetrazoles with carbodiimides generates products arising from the 1, 2-rearrangement or [1, 5]-C–H bond insertion of a putative alkylidenecarbene. Formation of this divalent intermediate is proposed to occur by way of a tetraazafulvene, which undergoes extrusion of 2 mol of dinitrogen. Details of this ...

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