SYNTHESIS OF STABLE BORYL-SUBSTITUTED DIAZOMETHANE AND NITRILIMINES

被引:23
作者
ARTHUR, MP
GOODWIN, HP
BACEIREDO, A
DILLON, KB
BERTRAND, G
机构
[1] CNRS,CHIM COORDINAT LAB,205 ROUTE NARBONNE,F-31077 TOULOUSE,FRANCE
[2] UNIV DURHAM,DEPT CHEM,DURHAM DH1 3LE,ENGLAND
关键词
D O I
10.1021/om00055a043
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Addition of bis(diisopropylamino)chloroborane to the lithium salt of (triisopropylsilyl)-, [bis(diisopropylamino)phosphino]-, and [bis(diisopropylamino)thioxophosphoranyl]diazomethane led to the corresponding stable N-borylnitrilimines 6-8 in 80, 90, and 95% yield, respectively. Addition of sulfur to C-phosphinonitrilimine 7 gave the thioxophosphoranyl analogue 8. The chloroborane reacted with the lithium salt of diazomethane, leading to a mixture of [bis(diisopropylamino)boryl]diazomethane (11) (54% yield) and bis[bis(diisopropylamino)boryl]nitrilimine (9) (20% yield). Compound 9 can be obtained in good yield by reacting the lithium salt of [bis(diisopropylamino]boryl]diazomethane with chloroborane. Photolysis of nitrilimines 6-9 afforded the corresponding carbodiimides 12-15. The regioselectivity and stereoselectivity of the 2 + 3 cycloaddition reactions of 6-8 with olefins were studied.
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页码:3205 / 3210
页数:6
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