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Radical-based transformation of vicinal diols to olefins via thioxocarbamate derivatives: a simple approach to 2',3'-didehydro-2',3'-dideoxynucleosides

Makoto Oba, Mitsuteru Suyama, Atsushi Shimamura and Kozaburo Nishiyama*

*Department of Material Science and Technology, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, Japan, Email:

M. Oba, M. Suyama, A. Shimamura, K. Nishiyama, Tetrahedron Lett., 2003, 44, 4027-4029.

DOI: 10.1016/S0040-4039(03)00847-5

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Bis-O-thioxocarbamate derivatives of vicinal diols are reduced with tris(trimethylsilyl)silane in the presence of azobisisobutyronitrile to afford the corresponding olefins in good yields. 2',3'-didehydro-2',3'-dideoxy analogs of adenosine, guanosine, inosine, cytidine and uridine were prepared.

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Radical-based deoxygenation of aliphatic alcohols via thioxocarbamate derivatives

M. Oba, K. Nishiyama, Tetrahedron, 1994, 50, 10193-10200. DOI: 10.1016/S0040-4020(01)81751-8

Key Words

Barton-McCombie reaction, Tris(trimethylsilyl)silane

ID: J72-Y2003-780