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

DOI	Resolve DOI: https://doi.org/10.1021/ol9913946
Author	Search for: Scaiano, J.C.; Search for: Martin, A.; Search for: Yap, G.P.A.; Search for: Ingold, K. U.¹
Name affiliation	National Research Council of Canada
Format	Text, Article
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	2000
In	Organic Letters 2, no. 7 (2000): 899–901.
Language	English
Peer reviewed	Yes
NPARC number	21276631
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Record identifier	12d1a166-4d2b-41ed-9032-ee5d5a39364d
Record created	2015-10-13
Record modified	2020-03-26