DL‐homoserinehydroxamic Acid, DL‐homo‐cystinedihydroxamic Acid, and Derivatives by Hydroxylaminolysis of γ‐Hydroxy‐ and γ‐Thio‐Lactones

The reaction of α‐amino‐, α‐carbamoylamino‐, α‐benzamido‐, and α‐benzyloxycarbonyl‐amino‐γ‐butyrolactone with hydroxylamine led to the formation of DL‐homoserinehydroxamic acid and α‐N‐acyl derivatives. α‐N‐Benzoyl‐DL‐homoserine‐N‐methyl‐hydroxamic acid and O‐benzylhydroxamic acid ester were prepared by reacting α‐benzamido‐γ‐butyrolactone with N‐methylhydroxylamine and with O‐benzylhydroxylamine, respectively. Hydroxyl‐aminolysis of DL‐homocysteinethiolactone and of N‐acyl‐DL‐homocysteinethiolactones gave homocystinedihydroxamic acid and N,N′‐disubstituted derivatives. Relative reactivities of O‐ and S‐lactones were compared.