Ring transformations in reactions of heterocyclic compounds with nucleophiles (XXI): Conversion of 5‐nitropyrimidine into pyridines and benzene derivatives by ketones

Abstract

and calculated values. the correlation coefficient being 0.993. The slope ofthe correlation line is 2.95. this is the multiplicative factor by which the values are related. This discrepancy can be ascribed to the Extended-Huckel method as shown by Hertdoii". The calculated net enthalpies of solvation in Table IV indicate that solvation indeed has an effect on the hydrolysis enthalpy. M o r r o r r r . rhis 1;&~1 is c~oii.sitli~rtrhlj~ Icirqer In the ciisi, o/' the hjdrolj~sis of c j~. l i c 3'5'-AMP t/iun,fiw the other phosphutc~ t/ic>ster.s. We will show t h t this i s diic to i i n rutrii .sttrbiliziition 01' thc. h~~lro1y.si.s product with rcspect t o the rcircrcrnts b j , h j~l r o~/ i~i i bondin</ with wtitrr rnolt~c~irlrs. Confi{/urutions 111111 hydroc/rti bonding ' See for part XX i n thc series on Riiig-transf~orrn~~ti~otis. li. C. i ' m r h P h , H . Jonyc,jmi and A. KorrtlIjs, J. Heterocycl. Chem. IS, 485 (1978). ' Part LXlX on Pyrimidines from this Laboratory; see for part LXVIII. J . P. G c~~r s and / I . C. i'tiii t l w Pltrs. J. Org Chem.. submitted (1978). J . C / i i r k . 13. Ptrrri-i and K. C o / m i i i . J. Chem. Soc.. Perkin 1. 1976. 1004: J . (./trrk. B. Ptrrrizi and J . 11: Soicihon, J. C'hern. Soc.. Perkin I . 1976, 125 and other papers in the series.' / I . ('. r t c i i tlcr P/tes. "Ring transformations of Heterocycles". Vols. I and 11. Academic Press (London and Ncw York). 1973. E. A. Oosii.ccri and / I . C'. i m i der Plrrs. Recl. l r a v . Chim. (Pays-Bas) 93, 233 (1974).