Tetrahedron letters

Thiones as superdipolarophiles

R Huisgen, E Langhals

Index: Huisgen, Rolf; Langhals, Elke Tetrahedron Letters, 1989 , vol. 30, # 39 p. 5369 - 5372

Full Text: HTML

Citation Number: 53

Abstract

Abstract According to kinetic measurements, the 1, 3-cycloadditions of diphenyldiazomethane to thioketones are much faster than those to α, β-unsaturated carbonyl compounds and nitriles previously regarded as record dipolarophiles. The primary cycloadducts are tetrasubstituted 1, 3, 4-thiadiazolines which extrude N 2 and furnish thiiranes via thiocarbonyl ylides.

Related Articles:

Nickel (O)-induced geminal bond cleavages leading to carbon-carbon double bonds: intermediacy of nickel (O)-carbene complexes as a unifying hypothesis

[Eisch, John J.; Qian, Yun; Singh, Mona Journal of Organometallic Chemistry, 1996 , vol. 512, # 1-2 p. 207 - 217]

Preparation and Reactivity of 1, 3-Bis (alkylthio) allenes and Tetrathiacyclic Bisallenes

[Shimizu, Toshio; Sakamaki, Kensuke; Miyasaka, Daisuke; Kamigata, Nobumasa Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1721 - 1728]

Preparation and Reactivity of 1, 3-Bis (alkylthio) allenes and Tetrathiacyclic Bisallenes

[Shimizu, Toshio; Sakamaki, Kensuke; Miyasaka, Daisuke; Kamigata, Nobumasa Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1721 - 1728]

Disparate Behavior of Carbonyl and Thiocarbonyl Compounds: Acyl Chlorides vs Thiocarbonyl Chlorides and Isocyanates vs Isothiocyanates

[Staudinger; Siegwart Helvetica Chimica Acta, 1920 , vol. 3, p. 838]

More Articles...