Yoshio Ueno

Carbocyclization by homolytic substitution (SH′ process). A new route to dihydroindole or dihydrobenzofuran

N-(4-Phenylthio-2-butenyl)-2-bromoaniline reacted with tributyltin hydride to give 3-vinyl-2,3-dihydroindole in 96% yield via hitherto unknown intramolecular SH′ process, some other examples and remarkable dilution effect on these homolytic carbocyclizations were described.

A novel homolytic substitution on vinylic carbon. A new route to vinyl stannane

Abstract (Alkylsulfonyl) benzothiazole 1 reacted with tributyltin hydride in the presence of azobisisobutyronitrile at 80°C to give 2-(tributylstannyl) benzothiazole in 67–79% yield. Similarly, vinylsulfone 4 gave the corresponding vinylstannane in 58–78% yield.

Radical cyclization via dichloromethyl radical. Stereoselective synthesis of cis-2,4-disubstituted pyrrolidine derivatives.

Abstract Allyl-2,2,2-trichloroethylamine derivatives 3 were cyclized via dichloromethyl radical to afford selectively cis-2,4-disubstituted pyrrolidine derivatives 4 by the treatment with tributyltin hydride under radical conditions.

Deoxygenation of allylic alcohols to terminal olefins via stannylation/destannylation☆

Abstract Deoxygenation of allylic alcohols to terminal olefins was performed via three steps; 1) [3,3]-sigmatropic rearrangement of O-allylxanthates, 2) the successive stannolysis with tributyltin hydride yielding allylic stannanes, and 3) final protolysis of allylic stannanes to terminal olefins.

β-Stannylpropionaldehyde. A versatile cyclopropane building-block

Abstract Various functional group-substituted cyclopropanes were prepared in good yield starting from β-tributylstannylproprionaldehyde via homoallylstannanes or γ-hydroxypropylstannanes.

A radical deoxygenation of secondary alcohols to hydrocarbons by use of tributyltin hydride

Abstract Secondary alcohols 1 reacted with 2,2′-dibenzothiazolyl- disulfide in the presence of tributylphosphine to give corresponding sulfides 2 in good yields. Sulfides 2 were subsequently desulfurized to hydrocarbons 3 with tributyltin hydride in radical conditions.

Stannes in synthesis: A new route to 2-substituted-1,3-butadienes via stereoselective allyltin formation under homolytic conditions☆

Abstract α-(Hydroxymethyl) allyl tolylsulfones reacted with tributyltin hydride in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene to give a allyltin derivatives which subsequently gave 2-substituted1,3-butadienes upon distillation in good yield.

A new method for the evaluation of the relative stability of organosulfur radicals by competitive elimination technique

Abstract The relative stability of various organosulfur radicals is estimated by competitive elimination technique using tributyltin radical and acetophenone derivatives having two different sulfur substituents at α and α positions.

A new method for the preparation of allylstannanes containing functional groups

Abstract Allylstannanes containing functional groups such as cyano, ester, or sulfonyl groups were prepared by the hydrostannolysis of the corresponding allylic sulfones with tri-n-butyltin hydride under neutral conditions.

Deacylative condensation I. A new facile method for the direct α-methylenation of ester or lactone starting from monosubstituted active methylene compounds

Bei der Behandlung mit Lithium-diisopropylamid (LDA), Paraformaldehyd und nachfolgender Pyrolyse erhalt man aus den Acetessigestern (I) die α-substituierten Acrylsauren (II).