SULFINIC ACIDS AND RELATED COMPOUNDS. 20. SYNTHESIS AND PROPERTIES OF SOME α, ω-ALKYLENEBIS(DITHIOALKANE-SULFINATES)

References

• 1986 . Presented in part at the Southeastern Regional Meeting of the American Chemical Society . Nov. 3–5 1986 , Louisville, Ky.
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• Macke , J. D. and Field , L. J. Org. Chem. , Paper 19 (in press)
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• May 1987 . May , Vanderbilt University . The doctoral dissertation of J. D. M., from which this paper was abstracted, can be consulted for further details
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• Bowman , G. T. , Clement , J. J. , Davidson , D. E. Jr. , Eswarakrishnan , V. , Field , L. , Hoch , J. M. , Musallam , H. A. , Pick , R. O. , Ravichandran , R. and Srivastava , P. K. 1986 . Chem.-Biol. Interactions , 57 : 161
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• H. A. Musallam of Walter Reed Army Medical Center . Unpublished data kindly provided by J. J. Clement of A. D. Little, Inc., through
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• Thus the peak of 1 at δ 1.62–1.73 for—CH2CH2SO2—(m,4H) was essentially unchanged in the salt 9 (n = 4). Half of the four peaks in 1 for—SSCH2CH2—(δ 1.76–1.88; m, 8H) remained for the salt 9 (n = 4) and half led to a new peak for 1,2-dithiane (6; 1.94–2.06, very broad singlet, the breadth attributable to 6 in suspension). The 2 × 2-H triplet for—CH2SO2—at δ 2.36–2.43 did not change significantly, while a multiplet for 4 ×—CH2SS—(8H, δ 2.74–2.86) separated into a peak for 1,2-dithiane at δ 2.84–2.92 (again a very broad singlet with fine structure; 4-H) and another at δ 2.77–2.82 for 2 ×—CH2SS of the salt 9 (n = 4)
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• The signal for—SSCH2(CH2)2CH2SS—of 3 at δ 1.78–1.84 (4H, m) virtually disappeared and a new signal appeared for it in the dithiane 6 (δ 1.98, m, 4H) under an existing 4H quintet for—O2SCH2CH2CH2S. The triplet for—O2SCH2—did not change significantly (4H, 2.42–2.48). Meanwhile, the signal for—SSCH2(CH2)2CH2SS—at δ 2.80 (t,4H) changed to that for 1,2-dithiane (6) under the existing triplet for—O2SCH2CH2CH2S at δ 2.84 (t, 4H). The final mixture thus showed the following resonances: δ 1.91–2.06 (appearance of a quintet, 8H) for—O2SCH2CH2CH2S and—SSCH2(CH2)2CH2SS—; 2.39–2.44 (t, 4H) for 2 × CH2SO2—; 2.78–2.94 (appearance of a triplet, 8H) for—SSCH2(CH2)2CH2SS, plus 2 × −O2S(CH2)2CH2SS
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