Tetrahedron p. 3437 - 3442 (1984)
Update date:2022-08-03
Topics:
Bartoli, G.
Bosco, M.
Cantagalli, G.
Dalpozzo, R.
The reduction of nitronate adducts from 1-methoxy-4-nitronaphthalene and Grignard reagents (CH3MgX, PhCH2CH2MgX, i-C3H7MgX, c-C6H11MgX and t-C4H9MgX) with hexamethyl phosphorous triamide and phosphorous trichloride 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-2,3-dihydro-1,4-naphthoquinone-1-oximes obtained after quenching with NH4Cl and HCl respectively.Oxime stereochemistry is assigned by LIS values caused by Eu(dpm)3 on (13)C signals of 2-methyl-4-methoxy-1-(2H)naphthalenone oxime and 2-methyl-2,3-dihydro-1,4-naphthoquinone-1-oxime.Complete reduction to amines is obtained with phosphorous trichloride.
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