SYNTHESIS AND REACTIONS OF ORGANIC-COMPOUNDS WITH A NITROGEN ATOM .10. SYNTHESIS OF ALLYLIC 1,2-DITOLUENE-SULFONAMIDE, 1,2-DIAMINE, HYDROXY-1,2-DITOLUENESULFONAMIDE AND HYDROXY-1,2-DIAMINE FROM (+)-ALPHA-PHELLANDRENE

Toluenesulfonamidation of (+)-alpha-phellandrene afforded 4-methyl-N-(1'-p-menthen-5'r,6'c-diyl)dibenzenesulfonamide 6 which was reduced by sodium in liquid ammonia to give the diamine 7. Hydroboration-oxidation of 6 followed by the sodium/ammonia reduction gave the diamine alcohol 9.