A facile ring cleavage of 3-aminothietane dioxides

✍ Scribed by Leo A. Paquette; Melvin Rosen

• Book ID: 104250130
• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 207 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99652-2

✦ Synopsis

The pronounced ability of sulfenes to add to electron-rich olefins by means of a cycloaddition pathway is now a well Imownphenomen~n.~ In particular, the addition of sulfenes to enamines has provided a valuable synthetic entry to 3-smindthietane dioxides.2 Such molecules, in contrast to J-sminocyclobutanones,3 are stable and have proven to.be key intermediates in the synthesis of various thiete sulfones. 4 We wish report preliminary results on a group of such compounds in which the proper disposition ?f a second substituent on the four-membered ring results in an extremely facile ring cleavqe reaction. to Addition of two equivalents of methsnesulfonyl chloride to a cold (-200) tetrahydrofuran solution of N,N,N',N'-tetramethylpropene-l,jdiamine (A)' snd triethylamine gave a dark oil which when chromatographeb on Florisil yielded in addition to the sulfonamide 2, m.p. &", e the vinylogous sulfonamides J_, m.p. 75&O, and 5, m.p. 69-70' (underlined atoms are those arising from the sulfene).' The structure of 2 followed from its infrared and n.m.r. spectra, and from its catalytic hydrogena-* Fellow of the Alfred P. Sloan Foundation