Sodium selenophenolate

Preparation of sodium selenophenolate. Reich et al. recommend the use of this reducing agent in place of sodium borohydride for preparation of sodium selenophenolate. 

Epoxide cleavage, Sodium selenophenolate reacts with the furanose 1, prepared from D-glucose, to form the diselenide 3 in quantitative yield. This reaction involves formation and cleavage of the epoxide 2, which can be also prepared by treatment of 1 with NaH. The epoxide is cleaved regiospecifically by attack from the less hindered side at C4. The phenylseleno group can be removed reductively by Raney nickel. The product was used to prepare isoepiallomuscarine (5). 

Sodium pyridylselenate, 368 Sodium selenophenolate, 368-369 Sodium succinimide, 78 Sodium sulfide, 377 Sodium thioethoxide, 368 Sodium triethylborohydride-Iron(H) chloride, 369... 

Cyclobutauones. Trost s original cyclobutanone synthesis (4, 211-214 definitive papers ) by rearrangement of oxaspiropentanes with lithium salts results in selective formation of the cyclobutanone in which the new carbon to carbonyl bond is introduced on the more sterically hindered face of the ketone. He and Scudder have now found that the isomeric cyclobutanone becomes the predominant product if the oxaspiropentane is rearranged through a selenoxide. An example is the rearrangement of 1. When lithium perchlorate is used the cyclobutanone 2 is obtained. On treatment with sodium selenophenolate followed by oxidation, the cyclobutanone 4 becomes the major product. In some cases this new selenoxide route is stereospecific and results in essentially only one cyclobutanone. 

LACTONES Lithium methyl mer-captide. Sodium selenophenolate. 

Sodium hydrogen carbonate, 457 Sodium hydrogen selenide, 459 Sodium hydrogen telluride, 459-460 Sodium hydrosulfite, 252 Sodium hydroxide, 460-461 Sodium methoxide, 463 Sodium p-methoxythiophenoxide, 421 Sodium 2-mcthyl-2-butoxide, 339 Sodium naphthalenide, 464 Sodium nitronates, 370, 371 Sodium selenophenolate, 212, 307, 397 Sodium sulfide, 360 Sodium tetracarbonylhydridoferrate, 419-420... 

Cyclopropyl nitriles are cleaved more efficiently by sodium selenophenolate. Example ... 

ALDEHYDES N Chlorosuccinimide. f-Leucine f-butyl ester. Lithium trimethylsilyl-diazomethane. Sodium selenophenolate. ThiphenoL 1-Trimethylsilyl-l.phenylselena-methyllithium. Zinc. 

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