SYNTHESIS AND REACTIONS OF ORGANIC-COMPOUNDS WITH A NITROGEN ATOM .11. THE REACTION OF LIMONENE WITH BIS(P-TOLUENESULFONYL)SELENODIIMIDE

Toluenesulfonamidation of(S)-(-)-limonene, (R)-(+)-limonene and dipentene gave (+/-)-4-methyl-N-[1',7'(8')-menthadien-4'-yl)benzenesulfonamide 8. Additionally (S)-(-)-limonene, (R)-(+)-limonene afforded the corresponding enantiomers of 4-methyl-N--[1',7'(8')-menthadien-9'-yl)benzenesulfonamide 9 and the racemic compound was obtained from dipentene. Reduction of toluenesulfonamides 8 and 9 by sodium in liquid ammonia gave the corresponding allylic amines 10 and 11.