Should Dithiophosphinate Esters Function as RAFT Agents?

Jennifer L. Hodgson, Katy A. Green, Michelle L. Coote

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

(Chemical Equation Presented) High-level ab initio calculations indicate that CH3 addition to the sulfur center of S=P(Z)(Z′)SCH3 (Z,Z′ = CH3, CN, OCH 3, Ph) is considerably less exothermic than addition to the corresponding RAFT agents, S=C(Z)SCH3. This suggests that dithiophosphinate esters may have only limited use in controlling free-radical polymerization, but should make excellent radical chain carriers in organic synthesis. The results cast doubt on the notion that phosphoranyl radicals are more "intrinsically" stabilized than carbon-centered radicals.

Original languageEnglish
Pages (from-to)4581-4584
Number of pages4
JournalOrganic Letters
Volume7
Issue number21
DOIs
Publication statusPublished - 1 Oct 2005
Externally publishedYes

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