✦ LIBER ✦

Peracid oxidation of imino ethers

✍ Scribed by Darryl Thomas; Donald H. Aue

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 159 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96245-8

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✦ Synopsis

The ready availability of imino ethers from alkylation of amides1 makes them attractive intermediates in the synthesis of new hetergcyclic compounds. We report here on the peracid oxidation of some strained and unstrained imino ethers to alkoxyoxasiranes and the reactivity of these new heterocycles.

2 Reaction of 0-methyl-N-t-butylformimidate, & with meta-chloro--perbenzoic acid (MCPHA) in dichloromethane at -20° gives 2-t-butyl-3-methoxyoxasirsne, 3 in 86% yield; bp 60~ (65 mm); ir (neat) 2970, 1480, 1410, 1370, 1280, 1150, 790 cm-'; nmr (CL&) 6 1.08 (s, 9H), 2.84 (s, JH), 5.17 (s, I-H); m/c 13~0946. This compound is stable to aqueous

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