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Original Articles

Selective access to sulfurated and selenated heterocycles by intramolecular cyclization of β-substituted sulfides and selenides

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Pages 172-174 | Received 20 Oct 2016, Accepted 20 Oct 2016, Published online: 26 Oct 2016

References

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  • a) Martynov, A. V.; Makhaeva, N. A.; Amosova, S. V. J. Sulfur. Chem. 2014, 35, 502-511. b) Xi, L.; Yi, L.; Jun, W.; Songsheng, Q. Thermochim. Acta. 2001, 375, 109-113.
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  • Degl'Innocenti, A.; Pollicino, S.; Capperucci, A. Chem. Commun. 2006, 4881-4893, and references cited therein.
  • Capperucci, A.; Tanini, D.; Borgogni, C.; Degl'Innocenti, A. Heteroatom Chem. 2014, 678-683.
  • Tanini, D.; Degl'Innocenti, A.; Capperucci, A. Eur. J. Org. Chem. 2015, 357-369.
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  • Characteristic data: Diastereomeric ratio = 60:40. 1H NMR (400 MHz, CDCl3), δ (ppm): 2.43–2.56 (4 H, m), 2.70–2.72 (4 H, m), 3.42–3.67 (4 H, m), 4.11–4.16 (1 H, m, CHCH2Cl), 4.41–4.44 (1 H, m, CHCH2Cl), 5.08 (1 H, bd, J = 9.3 Hz, CHOH), 5.21 (1 H, bd, J = 7.7 Hz, CHOH). 13C NMR (100 MHz, CDCl3), δ (ppm): = 18.5, 21.5, 29.6, 30.3, 47.2, 47.3, 78.4, 80.6, 96.9, 99.8.
  • Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron. 2007, 63, 5482-5489.

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