Methyl tributylstannyl sulfide

Methylthiooxindoles, 105 Methylthiotrimethylsilane, 352 Methyl tributylstannyl sulfide, 352-354 Methyl trifluoromethanesulfonate, 340 Methyl 3-(3,4,5-trimethoxyphenyl)-... 

See also 2,3-Bis(trimethylstannyl)-l,3-butadiene 4-Chloro-2-trimethylstannyl-l-butene (E)-l-Lithio-2-tributylstannyleth-ylene Methyl Tributylstannyl Sulfide trans-l,2-bis(tributy-lstannyl)ethylene Tributylstannylacetylene TributylstannyT copper Tributylstannylllthlum Trimethylstannylcopper-... 

The present radical formation was then applied to intramolecular cyclization. 3-Substituted cyclohexenone derivative 64 which has a (tributylstannyl)methylthio group in the side chain was irradiated (hv > 300 nm) in methanol. The desired spiro compound 65 was, however, obtained in low yield (23%) along with methyl sulfide 66 (60%) and dienone 67 (S%). In contrast, when 64 was irradiated in the presence of a 0.3 molar amount of 1,4-dicyanonaphthalene (DCN) as sensitizer in acetonitrile with 5 molar amounts of water, spiro ketone 65 was produced in 84% yield without a detectable amount of 66 and 67. Thus, by employing the DCN-mediated one-electron oxidation, the intramolecular coupling reaction proceeds smoothly (Scheme 27). 

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