Aminomethylenemalonates and Their Use in Heterocyclic by Alan R. Katritzky (Eds.)

By Alan R. Katritzky (Eds.)

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P. 293 (1975). N. Sonoda, N. Miyoshi, and S. Murai, Chem. Scr. 8A, 109 (1975). N. Miyoshi, S. Murai, and N. Sonoda, Tetrahedron Lett. p. 851 (1977). D. H. Olson, Tetrahedron Lett. p. 2053 (1966). 44 HANS J. REICH Similar adducts were isolated by Javaid, Sonoda, and T s u t s u m i . Although these authors assigned the selenoxide structure to their adducts, it is probable that the compounds were not selenoxides since they were eluted from silica gel with benzene (selenoxides are highly polar c o m p o u n d s and m e t h a n o l ether mixtures are normally necessary for chromatography on silica gel).

Organoselenium Oxidations 59 TABLE V PREPARATION OF OC-SELENOACETONE AND ACETOPHENONE BY DIRECT SELENENYLATION Selenenyl compound Derivative Yield of selenide (%) Ref. -TV Z = CH —C-Ph 87 88 2 SeZ SCN SCN OCH3 N0 N0 OCH3 2 2 126a 126a SeZ 74 CI 128 Sharpless, Lauer, a n d T e r a n i s h i have developed a procedure for the selenenylation of ketones a n d even aldehydes using PhSeCl a n d found that the reaction is compatible with the presence of a n u m b e r of functional groups including olefins a n d esters.

Wipff, and J. Demuynck, Helv. Chim. Acta 60, 1239 (1977). A. I. Shatenshtein and H. A. Gvozdeva, Tetrahedron 25, 2749 (1969); F. G. Bordwell, et al. J. Org. Chem. 42, 326 (1977). H. J. Reich, I. L. Reich, and J. M. Renga, J. Am. Chem. Soc. 95, 5813 (1973). D. L. J. Clive, Chem. Commun. p. 695 (1973). 9 1 2 2 1 2 3 58 HANS J. REICH The preparation of α,β-unsaturated carbonyl compounds using sulfoxide eliminations has been studied by T r o s t (see Seebach and T e s c h n e r for a recent review of keto sulfide chemistry).

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