Mhn. Arsanious, The reaction of Wittig and Wittig-Horner reagents and alkyl phosphites with 1,2-naphthoquinone-1-benzimide, MONATS CHEM, 130(7), 1999, pp. 921-928
Carbomethoxymethylene and carbethoxymethylene triphenylphosphoranes (1a, b)
react with 1,2-naphthoquinone-1-benzimide (8) to give the corresponding 1-
benzoylimino-1H-naphthalen-2-ylidene-acetic esters 9a,b and 2-(1-benzoylami
no-naphthalen-2-yl)-but-2-enedioic eaters 10a,b together with 1-benzamido-2
-naphthol (11). Application of Wittig-Homer reagents 4a,b on 8 at room temp
erature and in the presence of alcoholic sodium alkoxide renders 2-(1-benzo
ylaminonaphthalen-2-yl)-3-phosphonylsuccinic esters 12a,b. Conducting the r
eaction in refluxing toluene and in the presence of sodium hydride led to t
he formation of 2-benzamido-naphthol-1-ethyl ether (13). 1-Benzamido-2-naph
thol (11) was also isolated from both reaction media. Trimethyl and dimethy
l phosphites (7a,b) react with 8 to 14 as the sole product. Mechanisms acco
unting for the formation of the new products are discussed, and the probabl
e structures of the products are presented based on analytical and spectros
copic data.