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 (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.
Priefer
Ronny
R
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Lee
Yoon Joo
YJ
Barrios
Fabiola
F
Wosnick
Jordan H
JH
Lebuis
Anne-Marie
AM
Farrell
Patrick G
PG
Harpp
David N
DN
Sun
Aiming
A
Wu
Shaoxiong
S
Snyder
James P
JP