Solvolysis of (Z)-5-Trimethylstannyl 2-Adamantyl p-Bromobenzenesulfonate: Mechanistic Implications of a Record-Breaking Secondary α-Deuterium Kinetic Isotope Effect for an SN1 Substrate-Reference-Cited by-同舟云学术

Solvolysis of (Z)-5-Trimethylstannyl 2-Adamantyl p-Bromobenzenesulfonate: Mechanistic Implications of a Record-Breaking Secondary α-Deuterium Kinetic Isotope Effect for an SN1 Substrate

Published:2003-05-22 Issue:13 Volume:68 Page:5399-5402
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Adcock William¹,Trout Neil A.¹,Vercoe David¹,Taylor Dennis K.¹,Shiner, V. J.¹,Sorensen Ted S.¹

Affiliation:

1. School of Chemistry, Physics, and Earth Sciences, Flinders University of South Australia, Adelaide, SA 5001, Australia, Department of Chemistry, University of Adelaide, Adelaide, SA 5001, Australia, Department of Chemistry, Indiana University, Bloomington, Indiana 47405, and Department of Chemistry, University of Calgary, Calgary, Alberta, T2NIN4, Canada william.adcock@flinders.edu.au

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo0300892

Reference30 articles.

1. Evidence for 2-fold hyperconjugation in the solvolysis of 5-(trimethylsilyl) and 5-(trimethylstannyl)-2-adamantyl sulfonates

2. Through-bond transmission of substituent effects in the bicyclo[2.2.2]octane ring system: solvolysis of 4-deuterio- and 4-metalloidal (M(CH3)3, M = silicon, germanium and tin)-substituted bicyclo[2.2.2]oct-1-yl p-nitrobenzenesulfonates and methanesulfonates

3. Benzynes, dehydroconjugated molecules, and the interaction of orbitals separated by a number of intervening sigma bonds

4. Interaction of orbitals through space and through bonds

5. Orbital Theory of Heterolytic Fragmentation and Remote Effects on Nitrogen Inversion Equilibria

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