The Facile Regeneration of the Cahbonyl Compounds from α-Ditsianes. the Reaction of Chlcramine-t with Substituted 1, 3-Ditsanes

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Abstract
Prior to 1965, when corey and Seebach reported the utility of 1,3-dithianes (I)as a synthetic intermediate, little interest had been shown in reactions of this class of compounds. A few instances in which spiro (m-dithianes) proved useful in synthesis had been reported. 2. Various methods for openig the m-dithiane ring have been employed including Raney nickel desulfurization 2b,c,bromine in acertic acid3a the NBS and NCS method3b. variations onthe method of Wolfrom (a mercuric salt and cadmium carbonate) developed for mercaptoles3c,various methods employing silver ion3d often in the presence of an oxidizing agent3e, boron trifluoride in the presance of mecuric oxide or mercuric acetate3f, and oxidation of the dithaine to the corresponding monosulfoxide followed by acid hydrolysis.3g With the Exception of Raney nickel desulforization, interest in cleavage of the d-dithiane ring centers around recovery of the carbonyl compound.