Importance of Entropy in the Diastereoselectivity of 5-Substituted 2-Methyladamant-2-yl Cations-Reference-Cited by-同舟云学术

Importance of Entropy in the Diastereoselectivity of 5-Substituted 2-Methyladamant-2-yl Cations

Published:2004-07-17 Issue:17 Volume:69 Page:5537-5546
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Filippi Antonello¹,Trout Neil A.¹,Brunelle Patrick¹,Adcock William¹,Sorensen Ted S.¹,Speranza Maurizio¹

Affiliation:

1. Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università di Roma “La Sapienza”, 00185 Roma, Italy, the School of Chemistry, Physics, and Earth Sciences, The Flinders University of South Australia, Adelaide, Australia 5001, and the Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo049481l

Reference30 articles.

1. For reviews on this topic, see the special issue: Chem. Rev.1999,99(5): (a) Kaselj, M.; Chung, W.S.; le Noble, W. J.Chem. Rev.1999,99(5), 1387. (b) Adcock, W.; Trout, N. A.Chem. Rev.1999,99(5), 1415.

2. Electrostatic vs Hyperconjugative Effects as Stereoinductive Factors in the Adamantane Ring System

3. Stereochemistry of 2-methyl- and 2-phenyl-2-adamantyl cations

4. Diastereofacial Selectivity in Reactions of 5-Substituted (X) Adamant-2-yl Cations: Manifestations of Electron Demand

5. Tertiary cyclohexyl cations. Definitive evidence for the existence of isomeric structures (hyperconjomers)

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