First regioselective iodocyclization of O-allylselenocarbamates

4-Alkyl-2-imino-1,3-oxaselenolanes were prepared in good yields with high regioselectivity under mild conditions by the reaction of selenocarbamates with I2 or NIS. The resulting 4-alkyl-2-imino-1,3-oxaselenolanes on dehydrohalogenation gave 4-alkylidene-2-imino-1,3-oxaselenolanes. The formation of the (Z)- or (E)-isomer of 4-alkylidene-2-imino-1,3-oxaselenolanes, strongly depends on the configuration of the double bond of O-allylselenocarbamates.

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