Resolution of cyclopentanol methylene proton signals with Eu(fod) 3

Complete resolution of the five different protons of cyclopentanol has been achieved with the use of the lanthanide shift reagent Eu(fod) 3 for the first time, which permits stereochemical differentiation of the cis- and trans-2,5- and 3,4-protons for mechanistic studies of elimination, solvolytic,...

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Bibliographic Details
Published inJournal of magnetic resonance (1969) Vol. 35; no. 1; pp. 13 - 17
Main Authors Takakis, Ioannis M, Rhodes, Yorke E
Format Journal Article
LanguageEnglish
Published Elsevier Inc 01.01.1979
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Summary:Complete resolution of the five different protons of cyclopentanol has been achieved with the use of the lanthanide shift reagent Eu(fod) 3 for the first time, which permits stereochemical differentiation of the cis- and trans-2,5- and 3,4-protons for mechanistic studies of elimination, solvolytic, and other reactions of the cyclopentyl system. The separated peaks are assigned (in order of increasing downfield shift) as: H 3- and H 4- trans, H 2- and H 5-trans, H 3- and H 4- cis, H 2- and H 5- cis, and H 1. An example of application of the technique to mechanistic study is presented in the formolysis of deuterated cyclopentanol.
ISSN:0022-2364
1557-8968
DOI:10.1016/0022-2364(79)90075-1