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).
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 01238, USA.
J P
JP
Donahue
R H
RH
Holm
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