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Does a sterically bulky group occupy the equatorial site in trigonal bipyramidal phosphorus?

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
6
Issue
2
Pages
145–148
Identifiers
PMID: 14723514
Source
Medline
License
Unknown

Abstract

[structure: see text] The sterically bulky tert-butyl group occupies an apical position in trigonal bipyramidal phosphorus in the compound [CH2(6-t-Bu-4-Me-C6H2O)2]P(t-Bu)(1,2-O2C6Cl4) in contrast to the occupation of an equatorial position by the small methyl group in [CH2(6-t-Bu-4-Me-C6H2O)2]P(Me)(1,2-O2C6Cl4); this observation contradicts the familiar "apicophilicity rules" for trigonal bipyramidal phosphorus. Low-temperature solution 31P NMR spectra of [CH2(6-t-Bu-4-Me-C6H2O)2]P(R)(1,2-O2C6Cl4) (R = Me, Et, and n-Bu) show the presence of more than two isomers.

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