Phenylthio -l- trimethylsilyl cyclopropane

Peterson Alkenation. l-Lithio-l-(trimethylsilyl)cyclopro-pane, derived from l-phenylthio-l-(trimethylsilyl)cyclopropane by reductive lithiation with lithium l-(dimethylamino)naphtha-lenide (LDMAN), condenses with aldehydes to give carhinols which are converted to alkylidenecyclopropanes under Peterson alkenation conditions (eq 1).  

Synthesis of Cyclobutanes. t-Chloroperbenzoic acid oxidation of l-phenylthio-l-(trimethylsilyl)cyclopropane furnishes 

A list of General Abbreviations appears on the front Erulpapers 

Alternative treatment of the sulfoxide with aldehydes in the presence of tetra-w-butylammonium fluoride gives the phenyl-sulflnylcarbinol and thence the phenylthiocarbinol following reduction. The two last-named compounds are intermediates in the synthesis of cyclobutanones and cyclobutenes, respectively (eqs 3 and 4).2h,2c,2e 

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