Intramolecular Electron Transfer Reactions Catalyzed by a-Oxo

LUKACH A. E.; MORRIS D. G.; SANTIAGO A. N.; ROSSI R. A.

AMER CHEMICAL SOC

Año: 1995 vol. 60 p. 1000 - 1000

p class="MsoNormal" style="MARGIN: 0cm 0cm 0pt; TEXT-ALIGN: justify; mso-layout-grid-align: none">Efficient intramolecular ET catalysis in SRNl reactions was observed when a carbonyl group is present in l-chlorobicyclo[2.2.llheptane in the alfa or beta position. l-Chloro-3,3-dimethyl-2-oxobicyclo-L2.2.lIheptane (1) and 4-chloro-1,7,7-trimethyl-2-oxobicyclo[2.2.ll heptane (4) reacted with diphenylphosphide ion (Ph2P-) as nucleophile in liquid ammonia under photostimulation to give the substitution products in good yields, together with very small amounts of the reduction product. The substi