Dicubyl Disulfide

Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-05, Vol.124 (20), p.5626-5627
Main Authors: Priefer, Ronny, Lee, Yoon Joo, Barrios, Fabiola, Wosnick, Jordan H, Lebuis, Anne-Marie, Farrell, Patrick G, Harpp, David N, Sun, Aiming, Wu, Shaoxiong, Snyder, James P
Format: Article
Language:English
Subjects:
Aliphatic compounds
Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds
Chemistry
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Organic chemistry
Organic compounds
Physics
Preparations and properties
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record (1.771 Å). In contrast to previous generalizations, density functional theory calculations predict a low S−S rotation barrier similar to that for t-BuSSBu-t. Low-temperature 13C NMR (600 MHz) confirms the prediction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja025823y