Studies on the synthesis of linear aliphatic compounds. Part 2. The realisation of a strategy for repeated molecular doubling.

Abstract

Routes from C₁₁ and C₁₂ starting-materials, obtainable free from near homologues, to compounds of doubled chain length have been explored as approaches to the synthesis of n-paraffins and of terminally mono- or bi-functional derivatives. Acetylene alkylation routes lead to problems with protecting groups, but the use of the Wittig reaction provides a method of molecular doubling convenient for repeated use, with the formation of chain-lengths rising in a geometrical progression. The general problems inherent in the synthesis of very long-chain paraffins are discussed, earlier work is reviewed, and criteria for success are suggested. A useful protecting group for hydroxyl, the tri-p-tolylmethyl (trimtyl) ether, is described.