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Issue 15, 2006
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Scrambling of the label in a fluorenylphosphonamidic [18O]-sulfonate during dissociative nucleophilic substitution (elimination–addition): a measure of the importance of preassociation

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Abstract

When R2CHP(O)(NEt2)OS18O2Ar (R2CH = 9-fluorenyl, Ar = p-tolyl) undergoes nucleophilic substitution (elimination–addition) with Et2NH (0.4 mol dm−3 in CHCl3) the phosphene intermediate R2C[double bond, length as m-dash]P(O)NEt2 recombines with the sulfonate leaving group (internal return), causing scrambling of the 18O label, more quickly than it diffuses away; efficient conversion into R2CHP(O)(NEt2)2 therefore depends on preassociation between the substrate and the nucleophile.

Graphical abstract: Scrambling of the label in a fluorenylphosphonamidic [18O]-sulfonate during dissociative nucleophilic substitution (elimination–addition): a measure of the importance of preassociation

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Article information


Submitted
15 May 2006
Accepted
14 Jun 2006
First published
28 Jun 2006

Org. Biomol. Chem., 2006,4, 2842-2844
Article type
Communication

Scrambling of the label in a fluorenylphosphonamidic [18O]-sulfonate during dissociative nucleophilic substitution (elimination–addition): a measure of the importance of preassociation

M. J. P. Harger, Org. Biomol. Chem., 2006, 4, 2842
DOI: 10.1039/B606871E

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