115041-48-0

Upstream product

• 101335-23-3 4-chlorobutyro-O-benzylhydroxamate 
• 5555-72-6 N-benzyloxycarbamic acid ethyl ester 
• 1284281-62-4 (3-benzenesulfonylpropyl)-N-benzyloxycarbamic acid ethyl ester 
• 1284281-77-1 3-benzenesulfonyl-1-benzyloxypyrrolidin-2-one 
• 622-33-3 N-benzyloxyamine 

Relevant academic research and scientific papers

A new approach to cyclic hydroxamic acids: Intramolecular cyclization of N-benzyloxy carbamates with carbon nucleophiles

N-Alkyl-N-benzyloxy carbamates, 2, undergo facile intramolecular cyclization with a variety of carbon nucleophiles to give functionalized five- and six-membered protected cyclic hydroxamic acids, 3, in good to excellent yields. This method can be extended to prepare seven-membered cyclic hydroxamic acids in moderate yields. The sulfone intermediates 3 from this study can be alkylated while the corresponding phosphonates have been shown to undergo HWE reaction. The α,β-unsaturated synthon, 8, prepared by thermal elimination of sulfoxide 3m, undergoes Michael addition with secondary amines. The usefulness of this approach to prepare polydentate chelators has been demonstrated by the synthesis of bis cyclic hydroxamic acids 12, 14, and 15.

REARRANGEMENT OF N-(p-TOLUENESULFONYLOXY)-2-PYRROLIDINONE

Base induced rearrangement of N-(p-toluenesulfonyloxy)-2-pyrrolidinone provides 3-(p-toluenesulfonyloxy)-2-pyrrolidinone by an apparent nitrogen analog of the Favorskii rearrangement.