ACETYLENIC ESTERS - PREPARATION AND MECHANISM OF FORMATION OF ALKYNYL TOSYLATES AND MESYLATES VIA TRICOORDINATE IODONIUM SPECIES

被引：146

作者：

STANG, PJ ^{[1
]}

SURBER, BW ^{[1
]}

CHEN, ZC ^{[1
]}

ROBERTS, KA ^{[1
]}

ANDERSON, AG ^{[1
]}

机构：

[1] DUPONT CO, EXPT STN, DEPT CENT RES & DEV, WILMINGTON, DE 19898 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1987年 / 109卷 / 01期

关键词：

D O I：

10.1021/ja00235a034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The preparation and characterization of the first acetylenic esters of any kind (alkynyl tosylates, RC.tbd.COTs, and mesylates, RC.tbd.COMs) is reported. A simple, two-step procedure, starting from commercially available iodosobenzene diacetate, was employed in the synthesis. The final step involved ligand-ligand coupling in a tricoordinate iodonium species, C6H5I-(OTs)C.tbd.CR, via metal complexing. X-ray data indicate an ionic structure for the precursor alkynylphenyliodonium tosylate, C6H5I+C.tbd.CC6H5 .cntdot. OTs. A metal assisted nucleophilic acetylenic displacement, via an addition-elimination process, is suggested as the most likely mechanism for this novel main group ligand-ligand coupling reaction.

引用

页码：228 / 235

页数：8

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