Journal of the Chemical Society. Perkin transactions I p. 2447 - 2454 (1987)
Update date:2022-07-29
Topics:
Igner, Eva
Paynter, Oliver I.
Simmonds, Derek J.
Whiting, Mark C.
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.
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