Dicubyl disulfide |
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| 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 |
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| Institution: | Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA. |
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| Abstract: | 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 A). 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 (13)C NMR (600 MHz) confirms the prediction. |
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