An efficient sequence for the one-carbon homologation of aldehydes and ketones to carboxylic acids 2, esters 3and amides 4 involves (1) the Horner-Emmons modification of the Wittig reaction using diethyl tert-butoxy(cyano)methylphos-phonate (EtO)2POCH(CN)O-t-Bu to afford α-tert-butoxyacrylonitriles 15, (2) the cleavage of the tert-butyl ether in 15 using zinc chloride in refluxing acetic anhydride to afford α-acetoxyacrylonitriles 16and (3) the hydroxide, alkoxide, or amine solvolysis of 16 to afford 2, 3, or 4, respectively, in 57-88% overall yield from the carbonyl compounds.
|Number of pages||5|
|Journal||Journal of the American Chemical Society|
|State||Published - 1977|
ASJC Scopus subject areas
- Chemistry (all)
- Colloid and Surface Chemistry