Electrophilic α-p-tolylhydrazonylation of tert-butyl alkanoates and tertiary alkanamides with tert-butyl p-tolylazo sulfide

Article abstract of DOI:10.1016/0040-4020(96)00219-0

The reactions of the enolates of tert-butyl alkanoates 2 and N,N-dialkylalkanamides 3 with tert-butyl p-tolylazo sulfide 1 in THF furnish good yields of the corresponding α-p-tolylhydrazonylated esters 4 and amides 5. Results are reported showing the possible transformation of 4 and 5 into the N-methylated derivatives 8 and 9 and the subsequent deblocking of the protected carbonyl function to the corresponding 2-oxoalkanoates 10 and 2-oxoalkanamides 11.