Lithium Diisopropylamide Solvated by Hexamethylphosphoramide: Substrate-Dependent Mechanisms for Dehydrobrominations

Lithium diisopropylamide-mediated dehydrobrominations of exo-2-bromonorbornane, 1-bromocyclooctene, and cis-4-bromo-tert-butylcyclohexane were studied in THF solutions and THF solutions with added hexamethylphosphoramide (HMPA). Rate studies reveal a diverse array of mechanisms based on mono-, di-,...

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Veröffentlicht in:	Journal of the American Chemical Society 2006-12, Vol.128 (48), p.15399-15404
Hauptverfasser:	Ma, Yun, Ramirez, Antonio, Singh, Kanwal Jit, Keresztes, Ivan, Collum, David B
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology General and physical chemistry Hempa - chemistry Hydrocarbons, Brominated - chemistry Kinetics and mechanisms Molecular Structure Organic chemistry Propylamines - chemistry Reactivity and mechanisms Solutions Solvents - chemistry Structure-Activity Relationship
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Zusammenfassung:	Lithium diisopropylamide-mediated dehydrobrominations of exo-2-bromonorbornane, 1-bromocyclooctene, and cis-4-bromo-tert-butylcyclohexane were studied in THF solutions and THF solutions with added hexamethylphosphoramide (HMPA). Rate studies reveal a diverse array of mechanisms based on mono-, di-, and trisolvated monomers as well as triple ions. The results are contrasted with analogous eliminations in THF in the absence of HMPA.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja060964b