Naturalproductman’s Blog

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Loss of 2 x N2 to form carbenes

Posted by naturalproductman on February 29, 2012

Duncan Wardrop and co-worker from the University of Illinois in Chicago have reported in Organic Letters on an interesting approach to form a carbene by presumably forming a tetraazafulvene intermediate, which breaks down to the carbene by losing two molecules of nitrogen (ie:  N2).  At first I wondered how scary this reaction is because of the gain of entropy, but it looks pretty straight forward:  they just add DIC (diisopropylcarbodiimide) to the tetrazole and then load the reaction mixture directly on a column for purification.

Loss of N2

OL paper

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