New reaction of trithioorthoacetates. Reaction with acylating reagents

✍ Scribed by Hojo, Masaru; Masuda, Ryoichi

• Book ID: 120604720
• Publisher: American Chemical Society
• Year: 1975
• Tongue: English
• Weight: 417 KB
• Volume: 40
• Category: Article
• ISSN: 0022-3263
• DOI: 10.1021/jo00895a040

✦ Synopsis

by preparing and chromatographing samples of the dinitrophenylhydrazones. Fractional crystallization of the crude mixture of 2,4-dinitrophenylhydrazones from ethanol gave a sample (mp 131-132') which did not depress the melting point of a known sample of cyclopropylacetaldehyde 2,4-dinitrophenylhydrazone.

Cyclopropyloxirane (3). Cyclopropanecarboxaldehyde, 7.0 g (0.10 mol), was stirred under nitrogen with 28.6 g (0.14 mol) of trimethylsulfonium iodide in 60 ml of dimethyl sulfoxide. A solution of 14.0 g of potassium tert-butoxide in 150 ml of dimethyl sulfoxide was added dropwise with stirring during 30 rnin while cooling. After stirring for an additional 15 min, 300 ml of water was added slowly while cooling with ice. The solution was extracted with ether (3 X 500 ml) and the extract was washed with water and dried over molecular sieves. Distillation on a Teflon spinning band column gave, after removal of ether and tert-butyl alcohol, 2.6 g of 3: bp 85-90° (lit.lzb bp 100'); NMR (neat) 6 0.1-0.4 (m, 4 H, cyclopropyl CHz), 0.5-0.8 (m, 1 H, cyclopropyl CH), 2.4-2.7 (m, 2 H, oxirane CHz), 2.1-2.3 (m, 1 H, oxirane CH).ls Anal.lg Calcd for C ~H B O :