Pyrolytic elimination reactions of sulfinate and sulfonate esters

Autor:	Jerry W. Cubbage, Ryan D. McCulla, William S. Jenks
Rok vydání:	2002
Předmět:	Ethylene Chemistry Organic Chemistry Ring (chemistry) Medicinal chemistry Elimination reaction chemistry.chemical_compound Sulfonate Nucleophile Yield (chemistry) Electrophile Organic chemistry Pyrolytic carbon Physical and Theoretical Chemistry
Zdroj:	Journal of Physical Organic Chemistry. 15:71-77
ISSN:	1099-1395 0894-3230
Popis:	The barriers to pyrolytic unimolecular elimination by ethyl methanesulfonate and ethyl methanesulfinate were calculated for both five-membered ring eliminations that yield acetaldehyde and six-membered ring eliminations that yield ethylene. The experimental observation that related sulfinates undergo the five-centered elimination and sulfonates the six-centered elimination is reproduced by the calculations and rationalized in terms of a nucleophilicity/electrophilicity matching issue in the former and a charge-separated transition state in the latter. Copyright © 2001 John Wiley & Sons, Ltd.
Databáze:	OpenAIRE
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