Insertion of a two sulfur unit into the S–S bond—tailor-made polysulfides
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Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference10 articles.
1. (a) Litaudon, M.; Guyot, M. Tetrahedron Lett. 1991, 32, 911–914; (b) Chenard, B. L.; Harlow, R. L.; Johnson, A. L.; Vladuchick, S. A. J. Am. Chem. Soc. 1985, 107, 3871–3879; (c) Ford, P. W.; Narbut, M. R.; Belli, J.; Davidson, B. S. J. Org. Chem. 1994, 59, 5955–5960.
2. (a) Harpp, D. N.; Smith, R. A. J. Org. Chem. 1979, 44, 4140–4144; (b) Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045–6053.
3. (a) Westphal, U.; Steudel, R. Phosphorus, Sulfur, and Silicon and Rel. El. 1992, 65, 151–155; (b) Steudel, R.; Kustos, M.; Munchow, V.; Westphal, U. Chem. Ber. 1997, 130, 757–764.
4. Williams, C. R.; Britten, J. F.; Harpp, D. N. J. Org. Chem. 1994, 59, 806–812.
5. (a) Pickering, T. L.; Saunders, K. J.; Tobolsky, A. V. J. Am. Chem. Soc. 1967, 89, 2364–2367; (b) Musorin, G. K.; Sedunova, O. V.; Gendin, D. V. Russ. Chem. Bull. 1998, 47, 363–364; (c) Steliou, K. Sulfur Transfer Reagents. M.Sc. Thesis, McGill University, 1975; (d) the product was positively identified by comparison with p-tolyl tetrasulfide separately prepared following a procedure from: Saville, R. W. J. Chem. Soc. 1958, 2880–2888; (e) Dodson, R. M.; Srinivasan, V.; Sharma, K. S.; Sauers, R. F. J. Org. Chem. 1972, 37, 2367–2372; (f) Williams, C. R.; Harpp, D. N. Tetrahedron Lett. 1991, 7651–7654; (g) 1H NMR (CDCl3) δ=4.42 (s, 4H), 7.1 (m, 10H); 13C NMR (CDCl3) δ=40.33, 127.24, 128.18, 128.63, 140,32, 141.26; m.p. 149–151°C. Crystal data for 16: C16H14S6, Mr=398.63, crystal dimensions 0.65×0.20×0.17 mm, monoclinic, space group P21/n, a=21.020(8), b=5.698(2), c=14.769(4) Å, β=93.37(3)°, V=1765.9(10) Å3, ρcalc=1.499 g/cm−3, T=293(2) K, Z=4, F(000)=824, λ(CuKα)=1.54056 Å (graphite monochromated), 2θmax=69.82°, 3329 measured reflections of which 2865 with I>2σ(I) were used for refinement; Rint=0.031, R1=0.0269, wR2=0.072, GOF=1.026; (h) Bartlett, P. D.; Ghosh, T. J. Org. Chem. 1987, 52, 4937–4934.
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