カサシマ　ヨシオ   YOSHIO KASASHIMA   笠嶋　義夫    所属   千葉工業大学  創造工学部 教育センター（創造工学部）    職種   教授
言語種別	英語
発行・発表の年月	2012/12
形態種別	学術雑誌
査読	査読あり
標題	Reaction of Olefins with Nitriles under Solvent-Free Conditions Using Molecular Iodine as a Catalyst in the Presence of Water
執筆形態	共著
掲載誌名	Journal of Oleo Science
掲載区分	国内
出版社・発行元	Japan Oil Chemist' Society
巻・号・頁	61(12),pp.715-721
著者・共著者	Yohko Hanzawa, Yoshio Kasashima, Kazuki Tomono, Takashi Mino, Masami Sakamoto, Tsutomu Fujita
概要	The reaction of olefins with nitriles using iodine as a catalyst under solvent-free conditions was investigated. The reaction of cycloolefins, such as cyclopentene and cyclohexene, with benzonitrile using iodine as a catalyst produced both amide and heterocyclic compounds. The reaction of chiral (+)-camphene with benzonitrile produced racemic N-isobornylbenzamide (N-((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)benzamide). This indicated that skeletal rearrangement of camphene as well as amidation occurred. The optimized conditions were determined to be as follows: temperature, 90 C; molar ratio of nitrile:alcohol:iodine:water, 1:5:0.2:1.0; and reaction time, 18 h. The yield was 87% under these conditions. The reaction of (+)-camphene also proceeded with the other aromatic and aliphatic nitriles to produce racemic isobornylamides. However, except for styrene, complex reactions occurred in the reactions of benzonitrile with other terpenic olefins.
ISSN	1345-8957