A carbon-centered radical unreactive toward oxygen: Unusual radical stabilization by a lactone ring

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DOIResolve DOI: http://doi.org/10.1021/ol9913946
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TypeArticle
Journal titleOrganic Letters
ISSN1523-7060
Volume2
Issue7
Pages899901; # of pages: 3
Abstract(equation presented) A lactone ring confers unusual stability to a diphenylmethyl-like radical that is virtually unreactive toward oxygen. Thus, the radical derived from HP-136 is about 10 000 times less reactive than typical carbon-centered radicals. A reversible reaction with oxygen is proposed by analogy with triphenylmethyl; however, the association constant is about 1000 times smaller for HP-136 than for triphenylmethyl. While the lactone ring greatly influences the reactivity, the spectroscopy of the HP-136-derived radical is in line with that expected for a substituted diphenylmethyl radical.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276631
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Record identifier12d1a166-4d2b-41ed-9032-ee5d5a39364d
Record created2015-10-13
Record modified2016-05-09
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