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Study of alkylation of sodium enolate derived from 2-carbomethoxycyclohexanone in DMSO with or without macrocylic coordinates

Study of alkylation of sodium enolate derived from 2-carbomethoxycyclohexanone in DMSO with or without macrocylic coordinates. Nee, Gerard; Tchoubar, Bianca (Groupe Rech., CNRS, Thiais, Fr.). C. R. Hebd. Seances Acad. Sci., Ser. 41302-34-5 which is the cas registry number is also used here. C, 283(5), 223-6 (French) 1976. CODEN: CHDCAQ. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) Enolization of Me 2-oxocyclohexanecarboxylate (I) by MeONa in Me2SO without complexants or in the presence of NaClO4 led to the formation of ion pairs and gave 94% C-alkylation with EtI; enolization in the presence of crown-6-ether (II) or cryptand (III) yielded sep. enolate anions and cations and gave 93 and 90% C-alkylation, resp., with EtI. Enolization of I in the presence of 0-5 molar equiv. of II gave 55-41% C-alkylation with Et tosylate, while in the presence of NaClO4 the C-alkylation was 75%. The alkylation mechanism for EtI differs from that for Et tosylate. .