Synthesis and reactions of organic compounds with a nitrogen atom. Part XVI. Reactions of (-)-4-chloro-3(10)-carene and(+)-10-chloro-3-carene with phenyltelluro- andc phenylselenosodium

Allylic chlorides react with phenylselenosodium (3) or phenyltellurosodium (4) followed by chloramine-T to give allylic toluenesulfonamides [1–2]. Previously [3], we reported the synthesis of optically active allylic toluenesulfonamides from the corresponding allylic - and -pinene chlorides. The reduction of allylic toluenesulfonamides with sodium in liquid ammonia affords allylic amines, which are useful synthetic precursors [4–8]. Comparing the reactivity of seleno- and telluroorganic compounds in a one-step toluenesulfonamidation reaction, we demonstrated that better results can be obtained using the telluroorganic compounds. In contrast to easy isolable allylic phenylselenides, allylic phenyltellurides are very unstable and undergo an air oxidation. The secondary allylic-pinene chloride in the reaction with phenylseleno- or phenyltellurosodium rearranges to give primary allylic phenylselenide or allylic phenyltelluride. Herein, we investigated the possibility of using the reactions of optically active allylic carene chlorides with phenylselenosodium or phenyltellurosodium to the synthesis of the corresponding optically active toluenesulfonamides and amines. (–)-4Chloro-3(10)-carene (1) and (+)-10-chloro-3-carene (2), described in our previous paper [9], were chosen for the study.