Toluenesulfonamidation of alpha-pyronene (1,5,5,6-tetramethyl-1,3-cyclohexadiene) afforded two toluenesulfonamides: N,N'-(1',5',5',6'-tetramethyl-3'-cyclohexan-1',2'-diyl)ditoluenesulfonamide (9) and 4-methyl-N-(4',5',6',6'-tetramethyl-2',4'-cyclohexadien-1'-yl)benzensulfonamide (12). Toluenesulfonamidation of beta-pyronene (1,2,6,6-tetramethyl-1,3-cyclohexadiene) gave N,N'-(3',4',5',5'-tetramethyl-3'-cyclohexen-1',2'-diyl)ditoluenesulfonamide (16). Allylic mono- and ditoluenesulfonamides 9, 12, 16, were reduced by sodium in liquid ammonia to corresponding allylic mono- and diamines 17, 18 i 19.
Allyl phenylselenides from terpene systems are convenient precursors for the synthesis of the terpene allyl alcohols and allyl methylcarbamates. Using optically active allyl phenylselenides corresponding optically active oxygen and nitrogen derivatives were obtained. A new one-step method of the allyl methylcarbamates synthesis from allyl phenylselenides was described.
The reaction of selected allylic alcohols with methanol, ethanol, n-propanol, isopropanol and tert-butanol in the presence of catalytic amounts of cerium(III) chloride are described. Allylic alkyl ethers, bis-allylic ethers and 1,3-dienes were obtained depending on the structure of the reacting alcohols .
Allylic chlorination of (+)-3carene (1) gave (-)-trans-4-chloro-3(10)-carene (2), (+)-10-chloro-carene (4) and 3,4-dichlorocarene (5). Chlorination was done by two methods: with t-butyl hypochlorite or N-chlorsuccinimide in the presence of catalytic amount of alpha, alpha'-azobisisobutylonitrile or benzoyl peroxide, UV irradiation and silica gel. Chlorination of (+)-2-carene (7) using these methods gave p-cymene (8), 1-isopropylene-4-methylbenzene (9) and dipentene (10).
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