Abstract
AbstractAn efficient synthetic strategy to obtain 1‐chloro‐Cs‐trishomocubane and 1‐chloro‐D3‐trishomocubane is described. 1‐Chloro‐Cs‐trishomocubane is synthesized by a regioselective Diels–Alder reaction, and B3PW91/6‐31G(d,p) calculations offer a plausible explanation of the reaction mechanism. Surprisingly, 1‐chloro‐Cs‐trishomocubane does not undergo an acid‐catalyzed rearrangement to form 1‐chloro‐D3‐trishomocubane and was obtained by chlorosulfation of Cookson's diketone. A possible mechanism of the reaction involving the formation of Cs‐ and D3‐trishomocubane nonclassical cations was proposed on the basis of a mechanistic [B3PW91/6‐31G(d,p) and MP2/cc‐pVDZ] study.
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