DECOMPOSITION OF ARILAZIDES AND P-TOSYLAZIDE BY THF/n-BUTYLLITHIUM. A NEW SOURCE OF DIAZOMETHANE

Article abstract of DOI:10.1016/S0040-4020(01)91123-8

Variously substituted arylazides, as well as p-tosylazide, when allowed to react at room temperature with THF previously treated with n-butyllithium, undergo a rapid decomposition affording the corresponding amines and formamides, together with diazomethane.This diazo transfer (with deformylation) reaction is thought to involve the enolate of the acetaldehyde generated by the known cycloreversion of THF in the presence on n-butyllithium.