Ethyl 2-(diisopropoxyphosphoryl)-2H-azirine-3-carboxylate, the first example of an azirine bearing simultaneously ester and phosphonate groups was generated in situ and reacted with a number of 1,3-dienes. Cycloadducts or their ensuing rearranged products were isolated in moderate yields.
Ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate, the first example of an 3-heteroamatic 2H-azirine has been prepared. The reaction of ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate with conjugated 1,3-dienes, under mild conditions and in the absence of Lewis acid catalyst, afforded cycloadducts in good yield and high stereoselectivity.
The 2H-azirine 1 acts as an effective radical acceptor for secondary and tertiary alkyl iodides mediated by triethylborane. The addition proceeds with high regio- and diastereo-selectivity.
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