113309-15-2Relevant articles and documents
The Synthesis of Long-chain Unbranched Aliphatic Compounds by Molecular Doubling
Paynter, Oliver I.,Simmonds, Derek J.,Whiting, Mark C.
, p. 1165 - 1166 (1982)
A convenient general synthesis, applicable to alkanes and terminally mono- and di-substituted alkanes of any chain length, is described; cyclododecanone is used as the starting material, and the C12 chain is doubled in length as often as required and adjusted first to a multiple of 12, and then to any desired length.
Studies on Synthesis of Linear Aliphatic Compounds. Part 2. The Realisation of a Strategy for Repeated Molecular Doubling.
Igner, Eva,Paynter, Oliver I.,Simmonds, Derek J.,Whiting, Mark C.
, p. 2447 - 2454 (2007/10/02)
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 prtotecting groups, but the use of the Wittig reaction provides a method of molecular doubling convenient for repeated use, with 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.