Phosphonyl transfer by the elimination-addition mechanism: accelerated formation of an alkylidineoxophosphorane (phosphene) intermediate when a P-O single bond is replaced by P-S

The phosphonochloridate R2CHP(O)(YEt)Cl (R2CH = fluoren-9-yl, Y = O or S) reacts with (Pr2NH)-N-i largely or exclusively by an elimination-addition mechanism; the three-coordinate phosphene intermediate R2C=P(O)YEt is formed ca. 10(3) times more easily when Y = S than when Y = O.

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 24; pp. 2896 - 2897
Main Author Harger, MJP
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.12.2004
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PHOSPHOROTHIOATE
MONOESTER
CENTERS
NUCLEOPHILIC-SUBSTITUTION
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Summary:The phosphonochloridate R2CHP(O)(YEt)Cl (R2CH = fluoren-9-yl, Y = O or S) reacts with (Pr2NH)-N-i largely or exclusively by an elimination-addition mechanism; the three-coordinate phosphene intermediate R2C=P(O)YEt is formed ca. 10(3) times more easily when Y = S than when Y = O.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/b412036a