Electrophilic substitution with allylic rearrangement (SE′) stereochemistry of trifluoroacetolysis of some cyclohex-2-enylmetal compounds

Wickham G., Young D. and Kitching W. (1988) Electrophilic substitution with allylic rearrangement (SE′) stereochemistry of trifluoroacetolysis of some cyclohex-2-enylmetal compounds. Organometallics, 7 5: 1187-1195.

Author Wickham G.
Young D.
Kitching W.
Title Electrophilic substitution with allylic rearrangement (SE′) stereochemistry of trifluoroacetolysis of some cyclohex-2-enylmetal compounds
Journal name Organometallics   Check publisher's open access policy
ISSN 0276-7333
Publication date 1988
Sub-type Article (original research)
Volume 7
Issue 5
Start page 1187
End page 1195
Total pages 9
Subject 1604 Human Geography
1605 Policy and Administration
Abstract A range of (4-alkylcyclohex-2-enyl)-, (5-alkylcyclohex-2-enyl)-, and (6-alkylcyclohex-2-enyl)silanes, (4-alkylcyclohex-2-enyl)-, (5-alkylcyclohex-2-enyl)-, and (6-alkylcyclohex-2-enyl)germanes, and (4-alkyl-cyclohex-2-enyl)-, (5-alkylcyclohex-2-enyl)-, and (6-alkylcyclohex-2-enyl)stannanes were cleaved to the cycloalkene (and R3MX) with trifluoroacetic acid-d in various solvents. Complete allylic rearrangement (γ-attack) was observed, and the preferred direction of delivery of the electrophile (formally D+) to the γ-carbon of the allylic triad was determined by detailed 1H, 13C, and 2H NMR analyses of the derived dibromides of the various alkyl-substituted cyclohexenes or by direct 2H NMR analysis and comparisons with 2H-substituted alkylcyclohexenes of established relative configurations. A highly preferred γ-anti mode of acidolysis is established for all systems, except for the trans-4-tert-butylcyclohex-2-enyl derivatives, such exception being ascribed to steric impedance of electrophile approach, promoting syn attack. Thus, overall, highly γ-regioselective and anti-stereoselective substitutions (SE′) are observed.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
Versions
Version Filter Type
Citation counts: Scopus Citation Count Cited 0 times in Scopus Article
Google Scholar Search Google Scholar
Created: Tue, 12 Jul 2016, 02:18:37 EST by System User