Dicubyl Disulfide

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• 作者：Ronny Priefer ; Yoon Joo Lee ; Fabiola Barrios ; Jordan H. Wosnick ; Anne-Marie Lebuis ; Patrick G. Farrell ; David N. Harpp ; Aiming Sun ; Shaoxiong Wu ; and James P. Snyder
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：May 22, 2002
• 年：2002
• 卷：124
• 期：20
• 页码：5626 - 5627
• 全文大小：55K
• 年卷期：v.124,no.20(May 22, 2002)
• ISSN：1520-5126

文摘

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.