TY - JOUR
T1 - A One-Carbon Homologation of Carbonyl Compounds to Carboxylic Acids, Estersand Amides
AU - Dinizo, Stephen E.
AU - Freerksen, Robert W.
AU - Pabst, W. Edward
AU - Watt, David S.
PY - 1977
Y1 - 1977
N2 - 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.
AB - 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.
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U2 - 10.1021/ja00443a033
DO - 10.1021/ja00443a033
M3 - Article
AN - SCOPUS:0042003199
SN - 0002-7863
VL - 99
SP - 182
EP - 186
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 1
ER -