Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Rearrangement of Cyclic Ethynylcarbinol. I. Meyer-Schuster Rearrangement of Ethynylborneol.
香川 みち子
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1959 年 7 巻 3 号 p. 306-315

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1. 4-Acetylborneol was synthesized by an indirect process and it was cofirmed that the Hurd-Christ's 2-acetyl-6-hydroxycamphane is 4-acetylborneol and one kind of Rupe reaction occurs in this case. 2. By heating 2-ethynylborneol with dilute hydrochloric acid, 2-camphanylidene-acetaldehyde was obtained, no unsaturated ketone having been found, which is a product of Rupe reaction. Therefore the Meyer-Schuster rearrangement occurs in this case. 3. 2-Camphanylideneacetaldehyde was obtained by standing 2-ethynylborneol with conc. formic acid at 40°, showing that it undergoes Meyer-Schuster rearrangement at 40°and Rupe reaction at high temperature. 4. 4-Acetylborneol, 2-ethynylcamphene, 2-acetylcamphene, 2-acetylborneol, 4-ethynylcamphene, 4-acetylcamphene, 4-acetylcamphor, 4-ethynylborneol, and 4-ethynylcamphor, presumed to be related with anionotropic rearrangement of 2-ethynylborneol, were synthesized and their properties were studied.
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© The Pharmaceutical Society of Japan
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