Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control.

Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Research Abstract Details 

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Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Abstract Text:

Siddhartha R Shenoy,Deborah M Smith,K A Woerpel,

The limitations of stereoelectronic models in assessing the stereoselective nucleophilic substitution reactions of cyclic oxocarbenium ions at high reaction rates are discussed. Evidence is provided suggesting that the diastereoselectivity of nucleophilic substitution reactions is attenuated at the limits of diffusion control. The low diastereoselectivities observed in the reactions of trimethylsilyl cyanide with five- and six-membered ring oxocarbenium ions are attributed to the high reactivity of the nucleophile and its reactions with these electrophiles at diffusion control rates.

Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Publishing Authors By Initials

SR Shenoy,DM Smith,KA Woerpel,

For similar organic chemicals: organosilicon compounds: trimethylsilyl compounds research abstracts see: organic chemicals: organosilicon compounds: trimethylsilyl compounds research

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Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of the American Chemical Society

VOLUME: 128

Page Numbers: 8671-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 5

MONTH: Jul

YEAR: 2006

Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Keywords Mesh Terms:

KEYWORDS: Trimethylsilyl Compounds

MESH TERMS: chemistry

Chemical & Substance for Abstract: Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control. Information

Substance Name: trimethylsilyl cyanide

Registry Number: 7677-24-9

Grant and Affiliation Information for Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control.

AFFILIATION: Department of Chemistry, University of California-Irvine, Irvine, CA 92697-2025, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM 61066

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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