Nuclear magnetic resonance studies of some 2-(group 4B)-substituted 1,3-dithianes

Drew G.M. and Kitching W. (1981) Nuclear magnetic resonance studies of some 2-(group 4B)-substituted 1,3-dithianes. Journal of Organic Chemistry, 46 3: 558-563.

Author Drew G.M.
Kitching W.
Title Nuclear magnetic resonance studies of some 2-(group 4B)-substituted 1,3-dithianes
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 1981
Sub-type Article (original research)
Volume 46
Issue 3
Start page 558
End page 563
Total pages 6
Subject 1605 Policy and Administration
Abstract A number of 1,3-dithianes substituted with trimethylsilyl, stannyl, and plumbyl groups at the 2-position have been synthesized and their 1H and 13C NMR spectra obtained. Examination of chemical shifts, low-temperature spectra, and metal-13C coupling constants in certain 2,2-disubstituted 1,3-dithianes lead to the conclusion that these metalloidal groups have a much greater equatorial preference (at C-2) in 1,3-dithiane than in cyclohexane. For example, trimethylplumbyl, with an A value of 0.7 kcal/mol in cyclohexane, has an A value at C-2 in 1,3-dithiane in excess of 2 kcal/mol, whereas for simple alkyl groups, comparable A values are found for both systems. These results are related to the very large equatorial preference (>6 kcal/mol) of a 2-lithio group in 1,3-dithiane. Inter alia it is shown that electrophilic substitution by trimethyltin chloride on 5-tert-butyl-2-lithio-1,3-dithiane proceeds with overall retention of configuration.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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