Synthesis of a stable iminium salt and propellane derivatives

被引：33

作者：

Nagase, Hiroshi ^{[1
]}

Yamamoto, Naoshi ^{[1
]}

Nemoto, Toru ^{[1
]}

Yoza, Kenji ^{[2
]}

Kamiya, Kenshu ^{[3
]}

Hirono, Shuichi ^{[1
]}

Momen, Shinobu ^{[4
]}

Izumimoto, Naoki ^{[4
]}

Hasebe, Ko ^{[4
]}

Mochizuki, Hidenori ^{[4
]}

Fujii, Hideaki ^{[1
]}

机构：

[1] Kitasato Univ, Sch Pharm, Minato Ku, Tokyo 1088641, Japan

[2] BRUKER AXS KK, Adv Xray Solut, Yokohama, Kanagawa 2110022, Japan

[3] Kitasato Univ, Sch Sci, Kanagawa 2288555, Japan

[4] Toray Industries Ltd, Pharmaceut Res Labs, Kanagawa 2488555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 20期

关键词：

D O I：

10.1021/jo801276z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of morphinan I with NaH and MsCl provided very stable iminium salt 7 possessing propellane skeleton. One of the synthesized iminium salts 7, isobutyl derivative 7b, was crystallized and its structure was determined by X-ray crystallography. The natural bond orbital analysis suggested that the stability of the iminium should result from the stereoelectronic effect (hyperconjugation) attributed to their own structures.

引用

页码：8093 / 8096

页数：4

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