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Paper | Regular issue | Vol 53, No. 2, 2000, pp.301-314
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8754
Olefin Metathesis Reactions of Some Aromatic Dienes with ortho- and meta- Disubstitution. Formation of 10-, 12-, 14-, and 17-Membered Cyclic Compounds and Isomerization of an Allylic Alcohol

Katsuyuki Nakashima, Rika Ito, Masakazu Sono, and Motoo Tori*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan

Abstract

Some aromatic dienes with ortho- and meta-disubstitution have been subjected to olefin metathesis reactions. Compounds having allylphenyl groups substituted at their ortho positions successfully cyclized into 12-, 14-, and 17-membered alkenes in moderate to good yields, while compounds having the same groups substituted at their meta positions and those having vinylphenyl groups substituted at their ortho positions afforded mainly polymers. o-Allylphenyl 5-hexenyl ether produced 10-membered cyclooxadecadiene in 7.5% yield.