Formation of Allenes by 1,4-Addition of Intermolecular Phosphane/Borane Frustrated Lewis Pairs to a Conjugated Enyne

被引：5

作者：

Feldhaus, Philipp ^{[1
]}

Wibbeling, Birgit ^{[1
]}

Froehlich, Roland ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Kehr, Gerald ^{[1
]}

Erker, Gerhard ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

SYNLETT | 2014年 / 25卷 / 11期

关键词：

phosphorus; boron; Lewis pairs; allenes; ELECTRONIC CONTROL; ADDITION-REACTIONS; NITRIC-OXIDE; ACTIVATION; CHEMISTRY; HYDROGENATION; REDUCTION; BEHAVIOR; H-2;

D O I：

10.1055/s-0033-1341071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The t-Bu3P/B(C6F5)(3) frustrated Lewis pair (6a) undergoes competing acetylene deprotonation (to give the phosphonium-alkenylborate salt 8) and 1,4-P/B FLP addition to the conjugated enyne 2-methylbutenyne to yield the zwitterionic allene derivative 9a. The less basic (o-tolyl)(3)P/B(C6F5)(3) system (6b) avoids the acetylene deprotonation pathway. The zwitterionic allene derivative 9b formed by 1,4-P/B FLP addition to the enyne is again a prominent reaction product; here competing 1,2-addition is observed to give the olefinic product 10. The allene derivatives 9a and 9b and their competing products 8 and 10 were characterized by X-ray diffraction.

引用

页码：1529 / 1533

页数：5

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