Tetrahedron

Diacetoxylation of conjugated dienes with thallium (III) acetate in acetic acid

S Uemura, H Miyoshi, A Tabata, M Okano

Index: Uemura, Sakae; Miyoshi, Haruo; Tabata, Akira; Okano, Masaya Tetrahedron, 1981 , vol. 37, p. 291 - 295

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Citation Number: 16

Abstract

The reaction of conjugated dienes such as 1, 3-butadiene, isoprene, 2, 3-dimethyl-1, 3- butadiene, 2, 5-dimethyl-2, 4-hexadiene, 1, 3-cyclopentadiene, and 1, 3-cyclohexadiene, with thallium (III) acetate in acetic acid at 10–65° for 0.5–15 hr affords an isomeric mixture of the corresponding diacetoxyalkenes (1, 2-and 1, 4-addition products) in 10–92% yields. The 1, 2-addition products are predominantly formed in all cases examined except the case of ...

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