Stereochemistry of trifluoroacetolysis and brominolysis of the cyclohexyl-tin bond

Olszowy H.A. and Kitching W. (1984) Stereochemistry of trifluoroacetolysis and brominolysis of the cyclohexyl-tin bond. Organometallics, 3 11: 1676-1683.

Author Olszowy H.A.
Kitching W.
Title Stereochemistry of trifluoroacetolysis and brominolysis of the cyclohexyl-tin bond
Journal name Organometallics   Check publisher's open access policy
ISSN 0276-7333
Publication date 1984-01-01
Sub-type Article (original research)
Volume 3
Issue 11
Start page 1676
End page 1683
Total pages 8
Subject 1604 Human Geography
1605 Policy and Administration
Abstract Trifluoroacetolyses of cis- and trans-(4-methylcyclohexyl)- and cis- and trans-(4-tert-butylcyclohexyl)triisopropylstannanes proceed stereospecifically with retention of configuration at carbon, on the basis of direct 2H NMR examination of the reactions. Brominolysis was conducted under various conditions, and electrophilic brominolysis (methanol solvent) is characterized by a fine energetic balance between inversion and retention pathways, with the former favored for equatorial and the latter for axial carbon-tin bonds. Free radical brominolysis yields a statistical mixture of the cis- and trans-4-alkylcyclohexyl bromides, a result appropriate for bromine atom transfer to a 4-alkylcyclohexyl free radical.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 28 Jun 2016, 13:38:56 EST by System User