The quasi-homo-anomeric interaction in substituted tetrahydropyranyl radicals: Structure and kinetics of formation

被引：20
作者：
Beckwith, ALJ [1 ]
Duggan, PJ
机构：
[1] Monash Univ, Dept Chem, Melbourne, Vic 3168, Australia
[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
来源：
TETRAHEDRON | 1998年 / 54卷 / 18期
关键词：
D O I：
10.1016/S0040-4020(98)00178-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The EPR spectra of 3-acyloxytetrahydropyran-2-yl radicals (8 and 9) indicate that these species preferentially adopt conformations in which the orientation of the eater group allows maximum overlap between the SOMO, the lone pair on the ring oxygen, and the sigma* orbital of the C-O bond. These observations support earlier proposals that the same type of stabilising interaction affects the conformations of more complex glycosyl radicals. The rates of formation of 7 and 8 from the corresponding aryl sulfides are affected by this "quasi-homo-anomeric" interaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：4623 / 4632
页数：10
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