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Abstract
Title compounds (1,3,4) having the structure NaO2S(CH2)nSS(CH2)mSS(CH2)nSO2Na were prepared with m[dbnd]4 and n[dbnd]3–5 by reaction of 1,4-butanedithiol with cyclic disulfide 1,1-dioxides. Products were prepared similarly where a hydrogen atom in the 2-and 3-positions of the (CH2)4 moiety was replaced with OH in erythro (12) and threo (14) relationships; careful exclusion of oxygen was necessary. The products 1, 3, and 4 when heated in D2O in the dark gave 1,2-dithiane (6) and the appropriate bissulfinate, [NaO2S(CH2)nS]2, apparently by a heterolytic mechanism. The relative stabilities (for m = 4) were n = 5 >> 3 > 4. Under UV light 1, 3, and 4 reacted more rapidly and at about the same rate as one another, apparently by a homolytic mechanism. The two dihydroxy products (12 and 14) were considerably less stable in solution than 1, 3, and 4 but underwent the same type of reaction, as shown by comparison of spectra of the products with those of authentic mixtures. At ca. 25°C, the half-survival time for 12 and 14 was only ca. 25 min, and change was complete after ca. 80 min. The reaction of 14 appeared to be concentration independent and therefore may be first order.