Trimethylstannylation of mono- and dichloroarenes by the S(RN)1 mechanism in liquid ammonia

SANTIAGO,A.N.; BASSO,S.M.; MONTANEZ,J.P.; ROSSI,R.A.

J. Phys. Org. Chem.

Año: 2006 vol. 19 p. 829 - 835

0894-3230

The photostimulated reaction of methyl 2,5-dichloro benzoate (1) or methyl 3,6-dichloro-2-methoxy benzoate (7) with -SnMe3 ions give good yields of the disubstitution products by the S(RN)1 mechanism in liquid ammonia. Conversely, in dark conditions, substrate 1 reacts with -SnMe3 ions to afford the mono- substitution products by the S(RN)1 mechanism. On the other hand, substrate 7 reacts with -SnMe3 ions in dark conditions to give mono-reduced product probably by a halogen metal exchange reaction. In addition, the photostimulated reaction of 2-chloro-N-4-ethyl-N-6-isopropyl-1,3,5-triazin-4,6- diamine (Atrazine, 11) with -SnMe3 ions affords the reduced and substitution products in liquid ammonia-DMSO as co-solvent.