Sohei Suga

Novel route to selenoketones from ketones by the use of bis(dimethylaluminum) selenide

Abstract Bis(dimethylaluminum) selenide, prepared in situ via transmetallation reaction of bis(trimethylsilyl) selenide with dimethylaluminum chloride, reacted with ketones in the presence of a diene to give Diels-Alder adducts of the corresponding selenoketones and the diene.

Intramolecular Diels-Alder reaction of selenoaldehydes

Abstract Intramolecular Dieis-Alder reaction of selenoaldehydes which were generated from bis(trimethylsilyl) selenide and dienals gave the corresponding bicyclic adducts.

Intramolecular Diels-Alder Reaction of Thioaldehydes

Abstract Intramolecular Diels-Alder reaction of thioaldehydes which were generated from bis(trimethylsilyl) sulfide and dienals gave the corresponding bicyclic adducts.

The participation effect of halogen atoms in stereospecific Friedel–Crafts alkylations

The Friedel–Crafts alkylation of benzene with optically active 1,2-, 1,3-, 1,4-, and 1,5-dihalogenoalkanes gave the corresponding primary phenylalkyl halides with a stereospecificity which depended primarily on the type of terminal halogen or the variation in carbon chain length.

Retentive Friedel-Crafts alkylation

The Friedel Crafts alkylation of benzene with R-(–)-2-chloro-1-phenylpropane gave R-(–)-1,2-di-phenylpropane with almost complete retention of configuration below room temperature.

The UV-light or Free-radical Induced Polymerization of Propylene Sulfide in the Presence of Maleic Anhydride

he UV-light or Free-radical Induced Polymerization of Propylene Sulfide (PS) in the Presence of maleic anhydride (MAH) has been studied. It was found that polythioether was the only product. No adduct of MAH to polythioether was formed. The polymer (F=12∼17) did not contain mercapto groups. The polymerization reaction seems to proceed cationically by the formation of a charge transfer complex of PS and MAH, as in the case of propylene oxide.

Reaction of Xylene Isomers with Ethylene Oxide in the Presence of Lewis Acid

塩化アルミニウム触媒下でo-,m-,p-各キシレンに酸化エチレンを反応させ, 対応するβ-キシリルエタノール, すなわちβ-(3,4-ジメチルフェニル)エタノール,β-(2,4-ジメチルフェニル)エタノール,β-(2,5-ジメチルフェニル)エタノールを主として得た。これらアルコールの収率は塩化アルミニウム・酸化エチレンのモル比0.9,反応温度0～5℃で最大であり,m-,o-キシレンとの反応のさい少量の異性体アルコールの生成を認めた。また副生する炭化水素はα,β-ビス-キシリルエタンで,反応温度が高い場合,触媒・酸化エチレンのモル比が大きい場合に多く生成した。塩化アルミニウム以外の触媒でも反応は進み, 四塩化スズ触媒では触媒・酸化エチレンのモル比1 . 5 で塩化アルミニウムの場合に匹敵する収率でアルコールを生成し,しかも炭化水素を副生しなかった。四塩化チタン触媒ではアルコールの収率ほ低いが,かなりの量のβ-キシリルエチルクロリドを生成した。