Susan Wollowitz -- PhD 1980

Scientific Career

Thesis Title Reactivity and Rearrangement of Selenoxides and Sulfoxides.
Research Summary Sue explored the comparative chemistry of selenoxides and sulfoxides. She, with some followup by Ken Yelm, found that the selenoxide [2,3]sigmatropic rearrangement was substantially more exothermic than that of sulfoxides (by at least 10 kcal/mol).

She discovered a very nice procedure for the regiospecific 1,4-dehydration of allyl alcohols using sequential [2,3]sigmatropic rearrangement of a sulfenate ester followed by a sulfoxide elimination, according to the following scheme.

  1. "Syn Elimination of Alkyl Selenoxides. Side Reactions Involving Selenenic Acids, Structural and Solvent Effects on Rates," H. J. Reich, S. Wollowitz, J. E. Trend, F. Chow and D. F. Wendelborn, J. Org. Chem. 1978, 43, 1697.

  2. "Conversion of Allyl Alcohols to Dienes by Sulfoxide and Selenoxide syn Elimination. Synthesis of PCB Arene Oxides," H. J. Reich, I. L. Reich and S. Wollowitz, J. Am. Chem. Soc. 1978, 100, 5981.PDF

  3. "The Selenenate-Selenoxide Equilibrium. Kinetics and Thermodynamics," in "Selenium in Biology and Medicine," J. E. Spallholz, J. I. Martin, and H. E. Ganther, Eds., H. J. Reich and S. I. Wollowitz, AVI Publishing Co., Inc., Westport, CT, 1981, p. 460.

  4. "Stable Selenenic Acids," H. J. Reich, W. W. Willis, Jr., and S. Wollowitz, Tetrahedron Lett. 1982, 23, 3319.

  5. "Conversion of Allyl Alcohols to l,3-Dienes by Sequential Sulfenate-Sulfoxide [2,3] Sigmatropic Rearrangement and Syn Elimination," H. J. Reich and S. Wollowitz, J. Am. Chem. Soc. 1982, 104, 7051. PDF

  6. "Kinetics, Thermodynamics, and Stereochemistry of the Allyl Sulfoxide-Sulfenate and Selenoxide-Selenenate [2,3] Sigmatropic Rearrangements," H. J. Reich, K. E. Yelm and S. Wollowitz, J. Am. Chem. Soc. 1983, 105, 2503.

  7. "Preparation of α,β-Unsaturated Carbonyl Compounds and Nitriles by Selenoxide Elimination." Hans J. Reich, Susan Wollowitz, Organic Reactions 1993, 44, 1. (Review)

Current Position Vice President, Chemical Technology
Web address: Cerus Company

Nathan, Sue, Carl and Martha in 1980

For comments, additions and corrections, send e-mail to Hans J. Reich