Reactions of phosphonamidic acids and phosphonamidothioic acids with alcohols: mechanistic differences revealed by differing responses to steric effects
The formation of RP(X)(OH)OR' (R=Pr-i or Bu-t, R'=Me or Pr-i) from RP(X)(OH) NHBut and R'OH in CDCl3 is insensitive to steric effects when X=S but not when X=O (>10(3) times slower with R=Bu-t, R'=Pr-i than with R=Pr-i, R'=Me), pointing to a dissociative elimination-addit...
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Published in | Chemical communications (Cambridge, England) no. 17; pp. 2200 - 2201 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
01.01.2003
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Subjects | |
Online Access | Get full text |
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Summary: | The formation of RP(X)(OH)OR' (R=Pr-i or Bu-t, R'=Me or Pr-i) from RP(X)(OH) NHBut and R'OH in CDCl3 is insensitive to steric effects when X=S but not when X=O (>10(3) times slower with R=Bu-t, R'=Pr-i than with R=Pr-i, R'=Me), pointing to a dissociative elimination-addition mechanism (metathiophosphonate intermediate) when X=S but an associative S(N)2(P) mechanism when X=O. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/b307206a |