3,4-Bis(1-adamantyl)-1,2-dithiete: the first structurally characterized dithiete unsupported by a ring or benzenoid frame.
The structure determination of 3,4-bis(1-adamantyl)-1,2-dithiete, (C10H15)2C2S2 or C22H30S2, reported herein is the first crystallographic characterization of a 1,2-dithiete molecule unsupported by a benzenoid frame. Two independent molecules exist in the asymmetric unit separated by a pseudo-inversion center. The S2C2 four-membered dithiete ring is planar, with a trapezoidal shape enforced by the longer disulfide bond [average 2.086 (2) A] compared with the olefinic bond [average 1.363 (6) A]. The adamantyl substituents differ from one another by adopting slightly different rotational conformations with respect to the dithiete ring. The quaternary C atoms of the adamantyl groups deviate only slightly from the plane of the dithiete ring (average displacement of 0.023 A).
Donahue
J P
JP
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 01238, USA.
Holm
R H
RH
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004220:Disulfides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
C115035:3,4-bis(1-adamantyl)-1,2-dithiete; D001555:Benzene Derivatives; D004220:Disulfides; D000218:Adamantane