- Dehydrative fragmentation of 5-hydroxyalkyl-1 h -tetrazoles: A mild route to alkylidenecarbenes
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The development of a mild, base-free method for the generation of alkylidenecarbenes is reported. Treatment of 5-hydroxyalkyl-1H-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 methodology, its application to the synthesis of combretastatin A-4, and an improved route to 5-hydroxyalkyl-1H-tetrazoles are described.
- Wardrop, Duncan J.,Komenda, John P.
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p. 1548 - 1551
(2012/06/05)
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