TY - JOUR
T1 - Proof of the imidoyl phosphate intermediate for oxidative phosphorylation in [18O]dimethylformamide solution
AU - Cohen, Jack S.
AU - Lapidot, Aviva
PY - 1967/12/1
Y1 - 1967/12/1
N2 - The bromine oxidation of 2-methylnaphthalene-1,4-diol diphosphate in anhydrous [18O]-dimethylformamide resulted in orthophosphate enriched in oxygen-18. Appropriate controls showed no exchange. The observed incorporation indicated 26% formation of the imidoyl phosphate intermediate, Me2N+=CH·O·PO3H-, derived by solvation of monomeric metaphosphate from P-O bond fission. The 2-methyl-1,4-naphthaquinone produced in this oxidation was also enriched in oxygen-18, corresponding to 5% formation of intermediate solvated ketal analogues from C-O cleavage. The [18O]-dimethylformamide was prepared by direct exchange with enriched water.
AB - The bromine oxidation of 2-methylnaphthalene-1,4-diol diphosphate in anhydrous [18O]-dimethylformamide resulted in orthophosphate enriched in oxygen-18. Appropriate controls showed no exchange. The observed incorporation indicated 26% formation of the imidoyl phosphate intermediate, Me2N+=CH·O·PO3H-, derived by solvation of monomeric metaphosphate from P-O bond fission. The 2-methyl-1,4-naphthaquinone produced in this oxidation was also enriched in oxygen-18, corresponding to 5% formation of intermediate solvated ketal analogues from C-O cleavage. The [18O]-dimethylformamide was prepared by direct exchange with enriched water.
UR - http://www.scopus.com/inward/record.url?scp=37049139422&partnerID=8YFLogxK
U2 - 10.1039/J39670001210
DO - 10.1039/J39670001210
M3 - Article
AN - SCOPUS:37049139422
SN - 0022-4952
SP - 1210
EP - 1213
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
ER -