Journal article
Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes
Journal of organic chemistry, Vol.58(24), pp.6843-6850
11/1993
DOI: 10.1021/jo00076a055
Abstract
Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the title tetraester 3 affords trans -1,4-dialdehyde 4a as the major product. Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups. The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a–c with excess DIBALH results in reduction of only one ester group. An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17. Stereochemical assignments are supported by X-ray crystallographic data.
Details
- Title: Subtitle
- Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes
- Creators
- Charles R DavisDale C SwensonDonald J Burton
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.58(24), pp.6843-6850
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00076a055
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 11/1993
- Academic Unit
- Chemistry
- Record Identifier
- 9984622746202771
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