9.4.2 Barton Decarboxylation

Thiohydroxamate ester (commonly referred to as a Barton ester) with tributytin hydride or t-butylmercaptan in the presence of a radical initiator undergoes decarboxylation to give alkanes. The driving for this reaction is the S-Sn bond formation.

 

Mechanism

Instead of direct reaction of oxygen with the acid chloride, the following occurs:

Decarboxylation

Examples: