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Issue 89, 2015
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Steric control of the in/out sense of bridgehead substituents in macrobicyclic compounds: isolation of new “crossed chain” variants of in/out isomers

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Abstract

Isomers of the cage like dibridgehead diphosphine P((CH2)14)3P (1) are treated with Ph3PAu(2,6-C6H3(Trip)2) (2 equiv.; Trip = 2,4,6-C6H2(iPr)3). With out,out-1, workup gives out,out-1·(Au(2,6-C6H3(Trip)2))2 (46%), as confirmed by a crystal structure. With in,out-1, crystallization affords not in,out-1·(Au(2,6-C6H3(Trip)2))2, but rather an out,out isomer in which one of the (CH2)14 segments threads through the macrocycle formed by the other two. Implications for mechanisms of interconversion of in,out isomers are analyzed.

Graphical abstract: Steric control of the in/out sense of bridgehead substituents in macrobicyclic compounds: isolation of new “crossed chain” variants of in/out isomers

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Publication details

The article was received on 08 Jul 2015, accepted on 28 Aug 2015 and first published on 08 Sep 2015


Article type: Communication
DOI: 10.1039/C5CC05620A
Chem. Commun., 2015,51, 16053-16056

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    Steric control of the in/out sense of bridgehead substituents in macrobicyclic compounds: isolation of new “crossed chain” variants of in/out isomers

    M. Stollenz, D. Taher, N. Bhuvanesh, J. H. Reibenspies, Z. Baranová and J. A. Gladysz, Chem. Commun., 2015, 51, 16053
    DOI: 10.1039/C5CC05620A

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