Source: http://reag.paperplane.io/00000295.htm
Timestamp: 2019-04-22 14:18:57+00:00

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Physical Data: mp 124-126 °C.
Analysis of Reagent Purity: depending upon the method of preparation, it may contain bis(phenylsulfonyl)methane and 1,1,3,3-tetrakis(phenylsulfonyl)propane as impurities. In a few cases, isomerization to (E)-1,2-bis(phenylsulfonyl)ethylene has been observed.2,3a The chemical shift of the vinyl protons is 7.19 ppm (CDCl3).
Handling, Storage, and Precautions: keep dry and refrigerated; potential alkylating agent; use in a fume hood.
Due to the polarization of the reagent, [2 + 2] cycloadducts and products arising from dipolar rearrangements have been observed in reactions with strained alkenes. Benzonorbornadiene is an example (eq 6).6a The desulfonylation reaction can be performed with Aluminum Amalgam or Sodium Amalgam in such a way as to obtain sequential mono- and bisdesulfonylation (see also 1,2-Bis(phenylsulfonyl)ethylene).
1. (a) Neplyuev, V. M.; Bazarova, I. M.; Lozinskii, M. O. RCR 1986, 55, 883. (b) De Lucchi, O.; Pasquato, L. T 1988, 44, 6755. (c) Simpkins, N. S. In Sulphones in Organic Synthesis; Pergamon: Oxford, 1993.
2. Neplyuev, V. M.; Bazavova, I. M. ZOR 1981, 17, 2231.
3. (a) Carpino, L. A. JOC 1973, 38, 2600. (b) Stetter, H.; Steinbeck, K. LA 1974, 1315.
4. Bazavova, I. M.; Neplyuev, V. M.; Lozinkii, M. O. ZOR 1983, 19, 83.
5. (a) Neplyuev, V. M.; Lozinskii, M. O. ZOR 1981, 17, 2232. (b) Bazavova, I. M.; Neplyuev, V. M.; Lozinskii, M. O. ZOR 1982, 18, 865. (c) Rao, K. Y.; Nagarajan, M. IJC(B) 1983, 22B, 519. (d) Bazavova, I. M.; Neplyuev, V. M. UKZ 1983, 49, 758. (e) Baker, W. R.; Condon, S. L.; Spanton, S. TL 1992, 33, 1573.
6. (a) De Lucchi, O.; Pasquato, L.; Modena, G. TL 1984, 25, 3643. (b) De Lucchi, O.; Pasquato, L.; Modena, G. TL 1984, 25, 3647. (c) Obrecht, D. HCA 1991, 74, 27. (d) Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. TA 1992, 3, 1003.
7. (a) Himbert, G.; Kosack, S. CB 1988, 121, 2053. (b) Himbert, G.; Faul, D. TL 1988, 29, 5355.
8. (a) De Lucchi, O.; Lucchini, V.; Pasquato, L.; Zamai, M.; Modena, G. G 1984, 114, 293. (b) Rao, Y. K.; Nagarajan, M. S 1984, 757. (c) Paquette, L. A.; Kesselmayer, M. A.; Künzer, H. JOC 1988, 53, 5185. (d) Haber, M.; Pindur, U. T 1991, 47, 1925.
9. (a) De Lucchi, O.; Fabbri, D.; Lucchini, V. SL 1981, 565. (b) De Lucchi, O.; Fabbri, D.; Lucchini, V. T 1992, 48, 1485.

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