Naphthalene (1) has been reductively protonated in a dry ammonia/cosolvent mixture at-33" C using Li, Na, K, and Mg. In addition to 1, 4-dihydro-, 1, 2-dihydro-, and 1, 2, 3, 4- tetrahydronaphthalene (2-4, respectively) substantial amounts (20-70%) of oligomeric compounds were formed in the case of Li and Na. The reactions have been followed in time in order to obtain insight into the influence of the metal on the reaction course. The results ...
