テルペン類の極性非プロトン溶媒を用いる酸化反応(第9報)
数種の双環及び鎖状モノテルペン炭化水素の極性非プロトン溶媒中での自動酸化
1983 年 32 巻 2 号 p. 113-117
詳細
1983 年 32 巻 2 号 p. 113-117
The autoxidation of Δ3-carene (1), camphene (2), cis-pinane (3), cyclofenchene (4), alloocimene (5), myrcene (6), and dihydromyrcene (7) in the presence of polar aprotic solvents [DMSO, DMF, sulfolane (SF) or ethylene carbonate (EC)] under O2 carrier gas have been investigated of various conditions.
The results obtained are as follows:
In DMSO, m-methyl acetophenone (10) (product ratio 58%) was obtained as the main product from (1).
In DMF, fenchone (17) and pino-campheol (18) were obtained as two main products from (3) at the good selectivity (80% and 82%) among the oxidation products.
In SF, camphor (13) was obtained as the main product from (4). In conditions, 2, 6-dimethyl-3, 7-octadien-2-ol (33) and 2, 6-dimethyl-1, 7-octadien-3-ol (34) were obtained as major two products from (7), amounting to 85% and 86% of the oxidation products under different temperatures.
In EC, camphenilone (12) was obtained from (2) as the main product with high selectivity (91%). β-Methylcamphenilone (21) (product ratio 86%) was obtained from (4). 5-Isopropyl-2-methyl-2, 4-cyclohexadien-1-ol (25) was obtained from (5) as the main product, amounting to 80% of the oxidation products under the best conditions. Myrcenol (30) was obtained at the high selectivity (86%) in all converted products from (6). 2, 6-Dimethyl-7-octen-3-on (32) and (34) were obtained as two main products from (7) at the high selectivity (87% and 86%) among the oxidation products under different temperatures.
