AN UNEXPECTED 1,2-ALKYL SHIFT WITHIN A CHELATE BONDED ORGANOALUMINUM-ENAMINE

被引：23

作者：

WISSING, E ^{[1
]}

JASTRZEBSKI, JTBH ^{[1
]}

BOERSMA, J ^{[1
]}

VANKOTEN, G ^{[1
]}

机构：

[1] UNIV UTRECHT,DEBYE INST,DEPT MET MEDIATED SYNTHESIS,PADUALAAN 8,3584 CH UTRECHT,NETHERLANDS

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1993年 / 459卷 / 1-2期

关键词：

D O I：

10.1016/0022-328X(93)86050-R

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The organozinc-enamines EtZn[R'N-CH=CH-N(Et)R'] (R=(t)Bu (1a), (t)pent (2a), (i)Pr (3a)) react with Et3Al via a transmetallation reaction to the corresponding organoaluminium-enamines Et2Al[R'N-CH=CH-N(Et)R'] (R'=(t)Bu (1c), (t)pent (2c)) and Et2Zn. Prior to the transmetallation reaction initial 1 : 1 zinc-enamine-trialkylaluminium adducts are formed. Compounds 1c and 2c are thermally unstable and rearrange via a 1,2-alkyl shift partly in combination with a hydrogen shift, to Et2Al[R'N=CH-C(H)R'-NEt] (R'=(t)Bu (1d), (t)pent (2d)) (70%) and Et2Al[R'N-CH2CR'=NEt] (R'=(t)Bu (1e), (t)pent (2e)) (30%). The driving force for the alkyl shift, which is restricted to tertiary alkyl groups, is release of steric strain in the five-membered NCCN aluminium chelate ring.

引用

页码：11 / 16

页数：6

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