The first synthesis of aromatic compounds carrying two 1-adamantyls on adjacent positions. 3,4-Di-1-adamantylthiophene, o-di-1-adamantylbenzene, and 4,5-di-1-adamantylpyridazine

Synthesis of 3,4-Diphenyl-Substituted Poly(Thienylene Vinylene), Low-Band-Gap Polymers via the Dithiocarbamate Route

“…In the second route (Scheme , steps i, ii , iii, and v) toward dichloride 5a , 3,4-diphenylthiophene 9a has first been synthesized via the method developed by Nakayama et al , The latter involves the synthesis of thiophenes with two substituents on the 3 and 4 positions. Starting from commercially available 2-bromoacetophenon 6 , the reaction with sodium sulfide nonahydrate (Na 2 S·9H 2 O) yields 1,5-diphenyl-3-thiapentane-15-dione 7 .…”

Synthesis of distorted molecules based on spatial control with icosahedral carboranes

“…The dihedral angle between C(1A)-(cage A)-C(1) and C(2)-C(1B) (cage B) is 26.7°and the C(3)-C(2)-C(1)-C(6) torsional angle is 12.6°. Other aromatic compounds with two bulky substituents on adjacent positions include 1,2-di(1- adamantyl)benzene (7), which has been prepared by oxidation of 3,4-di(1-ada-mantyl)thiophene followed by Diels-Alder reaction with phenyl vinylsulfone [16]. Some geometrical parameters for 7 have been described in the literature [16] as preliminary results.…”

“…Other aromatic compounds with two bulky substituents on adjacent positions include 1,2-di(1- adamantyl)benzene (7), which has been prepared by oxidation of 3,4-di(1-ada-mantyl)thiophene followed by Diels-Alder reaction with phenyl vinylsulfone [16]. Some geometrical parameters for 7 have been described in the literature [16] as preliminary results. The corresponding values reported for 7 are 16.6°for C(1(Ad))-C(1) and C(2)-C(1(Ad)), and 7.1°for the C(3)-C(2)-C(1)-C(6) torsional angle.…”

Oxidation of congested thiophene 1,1‐dioxides with m‐chloroperbenzoic acid. Formation of epoxides and thiete 1,1‐dioxides and steric acceleration

“…These findings prompted us to examine the rn-CPBA oxidation of a series of congested thiophene dioxides, with emphasis being placed on the effect of bulky substituents on the rate of oxidation [7]. Thiophene 1 ,I-dioxides 3a [8] and 3b [9] were prepared as previously reported by us. Thiophene dioxide 3c was synthesized by rn-CPBA oxidation of 2,4-di-t-butylthiophene which could be obtained by isomerization of the easily available 3,4-di-t-butylthiophene.…”