Metal-Ammonia Reduction of Naphthalene at -33 deg C: Formation of Oligomeric Compounds

Article abstract of DOI:10.1021/jo00359a003

Naphthalene (1) has been reductively protonated in a dry ammonia/cosolvent mixture at -33 deg 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 (20-70percent) 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 indicate that the oligomerization proceeds via an anionic reaction mechanism by attack of the naphthalene monoanion onto the olefinic bond of 1,2-dihydronaphthalene.