The Journal of Organic Chemistry

Organic sulfur chemistry. 38. Desulfurization of organic trisulfides by tris (dialkylamino) phosphines. Mechanistic aspects

DN Harpp, DK Ash, RA Smith

Index: Harpp, David N.; Ash, David K.; Smith, Roger A. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5155 - 5160

Full Text: HTML

Citation Number: 26

Abstract

Tris (dialky1amino) phosphines effect a rapid desulfurization of trisulfides to disulfides under mild conditions. The reaction mechanism involves a bimolecular process, proceeding by the rate-determining formation of a phosphonium salt intermediate. The central sulfur atom of a diary1 trisulfide is removed in the process, while a dialkyl trisulfide loses a terminal sulfur atom to the aminophosphine.

Related Articles:

Mechanistic Insights into the Interface??Directed Transformation of Thiols into Disulfides and Molecular Hydrogen by Visible??Light Irradiation of Quantum Dots

[Li, Xu-Bing; Li, Zhi-Jun; Gao, Yu-Ji; Meng, Qing-Yuan; Yu, Shan; Weiss, Richard G.; Tung, Chen-Ho; Wu, Li-Zhu Angewandte Chemie - International Edition, 2014 , vol. 53, # 8 p. 2085 - 2089 Angew. Chem., 2014 , vol. 126, # 8 p. 2117 - 2121,5]

Synthesis of Diaryl Disulfides via Mild Reduction of Arylsulfinates with Hydrazine Monohydrate in DMSO

[Zhu, Rui-Heng; Shi, Xiao-Xin Synthetic Communications, 2012 , vol. 42, # 8 p. 1108 - 1114]

Vinylic cations from solvolysis. 33. Solvolysis of E-and Z-1-anisyl-2-(p-nitrophenyl) propen-1-yl chlorides

[Rappoport, Zvi; Pross, Nella Journal of Organic Chemistry, 1980 , vol. 45, # 22 p. 4309 - 4320]

Synthesis and reactivity of dipropargylic disulfides: tandem rearrangements, cyclization, and oxidative dimerization

[Braverman, Samuel; Cherkinsky, Marina; Meridor, David; Sprecher, Milon Tetrahedron, 2010 , vol. 66, # 10 p. 1925 - 1930]

. beta.-Cyano-and. beta.-carbethoxy sulfides, sulfoxide, and sulfones and their Knoevenagel condensation

[Dressler,H.; Graham,J.E. Journal of Organic Chemistry, 1967 , vol. 32, p. 985 - 990]

More Articles...