Chain extension with <i>tert</i>‐butyl lithioacetate

Abstract

Abstract Iodides containing methylene‐interrupted triple or double bonds can be chain‐extended in 45‐73% yield by reaction with tert ‐butyl lithioacetate in THF/HMPT at −35°C and subsequent acid‐catalyzed thermolysis at 100°C. Alkyl and allyl bromides or iodides give acids in yields of 60 to 89%. In some cases, minor amounts of methyl ketones were found. Alkyl chlorides and alkyl methane‐, benzene‐ or p ‐toluenesulphonates are not suitable.