The Reaction of Organoboranes with Ethyl P-Nitrobenzenesulfonoxy-Carbamate Under Two-Phase Conditions. A Convenient Synthesis of Ethyl N-Alkylcarbamates from Olefins via Hydroboration

Abstract

Organoboranes readily obtainable from olefins via hydroboration have been shown to be versatile synthetic reagents and intermediates.¹ Many reports have appeared dealing with the syntheses of primary,² secondary,³ and tertiary⁴ amines from organoboranes. On the other hand, there are a few examples of the similar reactions leading to nitrogen compounds possessing substituents other than hydrogen or alkyl groups attached to nitrogen. It was known that the reaction of organoboranes with iron(III) azide in the presence of hydrogen peroxide gives corresponding azidoalkanes,⁵ and N-alkylsulfonamides⁶ are prepared via the reaction of organoboranes with chloramine-T and its analogues.