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The nature of the electronic factor governing diastereofacial selectivity in remotely substituted (X) 2-adamantyl cations: 5-X versus 4-X substitution by William Adcock; Neil A. Trout is a Chemistry article available to read on EtoBox.

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## Abstract A limited series of 4^eq^‐substituted (X) 2‐methyleneadamantanes (6, YCH~2~, XF, Cl, Br, I, and SnMe~3~) has been synthesized and diastereoselectivities for their hydrochlorination (HCl/CH~2~Cl~2~) have been determined. Diastereoselectivities for the fluorination (DAST/CH~2~Cl~2~) of __secondary__ alcohol mixtures, obtained from the hydride reduction of the precursor ketones (6,YO) to the alkenes, have also been measured. A comparison of this selectivity data for nucleophilic trapping of 4^eq^‐substituted (X) 2‐adamantyl cations (4, RH and Me) with the corresponding information for 5‐substituted (X) 2‐adamantyl cations (1, RH and Me) has revealed important distinctions between the two series. In particular, whereas extended hyperconjugative effects appear to be the predominant electronic effect governing facial selectivity in the 5,2‐series, electrostatic influences prevail in the 4,2‐disposition. Copyright © 2007 John Wiley & Sons, Ltd.

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Author

William Adcock; Neil A. Trout

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0894-3230)

Published

2007

Language

EN

Field

Chemistry (Physical Sciences)