Theoretical and experimental study on the in-plane SN2-type substitution reaction of haloalkenes with inversion of configuration at the sp2 carbon

被引：32

作者：

Ando, K ^{[1
]}

Kitamura, M

Miura, K

Narasaka, K

机构：

[1] Univ Ryukyus, Coll Educ, Okinawa 9030213, Japan

[2] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 14期

关键词：

D O I：

10.1021/ol049119t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular in-plane S(N)2 type reaction of haloalkene E-8a was predicted to be a facile process for the first time by DFT calculations (B3LYP/6-31+G(d),SCRF(dipole, solvent = DMF)) (DeltaG = 14.4 kcal/mol). The prediction was confirmed experimentally. When E-8a was treated with NaH in DMF, benzofuran was obtained in 95% yield. On the other hand, Z-8a was recovered quantitatively even after heating at 110 degreesC.

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页码：2461 / 2463

页数：3

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