Reactions of 1- and 2-Halo and 1,2-Dichloroadamantanes with Nucleophiles by the SRN1 Mechanism

SANTIAGO A. N.; STAHL A. E.; RODRIGUEZ G. L.; ROSSI R. A.

AMER CHEMICAL SOC

Año: 1997 vol. 62 p. 4406 - 4406

p class="MsoNormal" style="MARGIN: 0cm 0cm 0pt; mso-layout-grid-align: none">ABSTRACT: The photostimulated reaction of methyl 2,5-dichloro benzoate (1) or methyl 3,6-dichloro-2-methoxybenzoate (7) with _SnMe3 ions give good yields of the disubstitution products by the SRN1 mechanism in liquid ammonia. Conversely, in dark conditions, substrate 1 reacts with -SnMe3 ions to afford the mono-substitution products by the SRN1 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-N4-ethyl-N6-isopropyl-1,3,5-triazin-4,6-diamine (Atrazine, 11) with -SnMe3 ions affords the reduced and