Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions - III. Reactivity of diaryl ketones, ethers, thioethers, sulfoxydes, and sulfones. An experimental and theoretical study

被引：20
作者：
Karady, S
Cummins, JM
Dannenberg, JJ
del Rio, E
Dormer, PG
Marcune, BF
Reamer, RA
Sordo, TL
机构：
[1] Merck & Co Inc, Merck Res Labs, Proc Res Dept, Rahway, NJ 07065 USA
[2] CUNY Hunter Coll, Dept Chem, New York, NY 10021 USA
[3] CUNY, Grad Sch, New York, NY 10021 USA
[4] Univ Oviedo, Dept Quim Fis & Analit, Oviedo 33006, Principado De A, Spain
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 08期
关键词：
D O I：
10.1021/ol027301t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Experiments show that free radical hydrogen shift is significant in the Pschorr cyclization of diphenyl ethers (X = O) and thioethers (X = S) and does not take place with sufoxides; (X = SO) and sulfones; (X = SO2). DFT calculations of the product ratios, activation energies, rate constants for H-transfers, and ring-closings at the UB3PW91/6-31G(d,p) level are in excellent agreement with the experimental results reported here and elsewhere in the literature.
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收藏
页码：1175 / 1178
页数：4
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