A Convenient Road to 1‐Chloropentacycloundecanes – A Joint Experimental and Computational Investigation | Zendy

Sharapa Dmitry I. | Zendy; Gayday Alexander V. | Zendy; Mitlenko Alena G. | Zendy; Levandovskiy Igor A. | Zendy; Shubina Tatyana E. | Zendy

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A Convenient Road to 1‐Chloropentacycloundecanes – A Joint Experimental and Computational Investigation

Author(s) -

Sharapa Dmitry I.,

Gayday Alexander V.,

Mitlenko Alena G.,

Levandovskiy Igor A.,

Shubina Tatyana E.

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201001731

Subject(s) - chemistry , regioselectivity , reaction mechanism , mechanism (biology) , computational chemistry , diketone , catalysis , stereochemistry , organic chemistry , physics , quantum mechanics

An efficient synthetic strategy to obtain 1‐chloro‐ C s ‐trishomocubane and 1‐chloro‐ D 3 ‐trishomocubane is described. 1‐Chloro‐ C s ‐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‐ C s ‐trishomocubane does not undergo an acid‐catalyzed rearrangement to form 1‐chloro‐ D 3 ‐trishomocubane and was obtained by chlorosulfation of Cookson's diketone. A possible mechanism of the reaction involving the formation of C s ‐ and D 3 ‐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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