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R. M. , and A. B. Smith, III, Tetrahedron Lett. p. 4361 (1977). P. A. Grieco, S. Gilman, and M. Nishizawa, J. Org. Chem. 41, 1485 (1976). D. Liotta, W. Markiewicz, and H. Santiesteban, Tetrahedron Lett. p. 4365 (1977). /. Organoselenium Oxidations 27 The nucleophilic opening of lactones can be carried out with uncomplexed P h S e N a in refluxing T H F / H M P A , or in D M F at 110°-120°C with reagent prepared by borohydride reduction of P h S e . The phenylseleno carboxylic acids so formed were esterified and converted to ω-olefinic esters by selenoxide syn elimination (see Table I).

112c) (ref. 112f) (ref. 112e) 1 1 2 b i l 2 c 1 1 2 d 1 1 2 e 1 1 2 f K. C. Nicolaou and Z. Lysenko, Tetrahedron Lett. p. 1257 (1977). K. C. Nicolaou and W. E. Barnette, Chem. Commun. 331 (1977). E. J. Corey, G. E. Keck, and I. Szekely, J. Am. Chem. Soc. 99, 2006 (1977). D. L. J. Clive, G. Chittattu, N. J. Curtis, W. A. Kiel, and C. K. Wong, Chem. Commun. p. 725 (1977). A. G. Gonzalez, C. Hernandez, J. A. Salazar, and E. Suarez, Tetrahedron Lett. p. 2959 (1977). 48 HANS J. REICH E. SELENIUM-STABILIZED ANIONS The formation of selenides and selenoxides by reaction of α-lithio organo­ selenium compounds with alkylating agents and carbonyl c o m p o u n d s provides versatile synthetic routes to olefins, dienes, and allyl alcohols.

Reich and I. L. Reich, unpublished results. P. H. D. Thesis, University of Wisconsin, Madison (1977); Β. M. Trost and P. H. Scudder, / . Am. Chem. Soc. 99, 7601 (1977). E. S. Gould and J. D. McCullough, J. Am. Chem. Soc. 73, 1109 (1951); D. DeFilippo and F. Momicchioli, Tetrahedron 25, 5733 (1969). 32 HANS J. REICH b. Reductions can be seen when selenols are formed under acidic condi­ tions. Pummerer-like processes, in which oxidation α to a selenoxide accom­ panied by reduction at selenium occurs, have been found for several types of selenides.

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