Reduction of nitronate adducts from RMgX and 1-hethoxy-4-nitronaphthalene to oximes or amines by trivalent phosphorus reagents
作者:G. Bartoli、M. Bosco、G. Cantagalli、R. Dalpozzo
DOI:10.1016/s0040-4020(01)91493-0
日期:1984.1
The reduction of nitronate adducts from 1-methoxy-4-nitronaphthalene and Grignard reagents (CH3 MgX, PhCH2CH2HgX, i-C3H7 MgX, c-C6H11MgX and t-C4H9MgX) with hexamethyl phosphorous triamide and phosphorous trichlorlde is reported. With the former reagent the reaction is chemio and stereoselective and only the E-oxime is recovered being the E-2-alkyl-4-methoxy-1(2H)naphthalenone oximes and the E-2-alkyl-2
用六甲基磷三酰胺和1-甲氧基-4-硝基萘和格氏试剂(CH 3 MgX,PhCH 2 CH 2 HgX,iC 3 H 7 MgX,cC 6 H 11 MgX和tC 4 H 9 MgX)还原亚硝酸盐加合物据报道三氯化磷。使用前一种试剂,该反应是化学和立体选择性的,仅回收了E-肟,即E-2-烷基-4-甲氧基-1(2H)萘酮肟和E-2-烷基-2,3-二氢-肟。分别用NH 4 Cl和HCl淬灭后获得的1,4-萘醌-1-肟。肟的立体化学由Eu(dpm)3引起的LIS值指定上13个2-甲基-4-甲氧基-1-(2H)萘酮肟和2-甲基-2,3-二氢-1,4-萘-1-酮肟的C信号。用三氯化磷将胺完全还原成胺。