Rearrangement of Cyclic Ethynylcarbinol. I. Meyer-Schuster Rearrangement of Ethynylborneol.

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概要

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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.

• 公益社団法人日本薬学会の論文
• 1959-05-10

著者

• 香川 みち子

  Institute Of Physical And Chemical Research

関連論文

• Rearrangement of Cyclic Ethynylcarbinols. III. A Few Supplementary Reaction with Monocyclic and Bicyclic Terpenoids.
• Anionotropic Rearrangement of Cyclic Ethynylcarbinol. II. The Epimeric Resolution and the Mechanism of Anionotropic Rearrangement of Ethynylborneol
• Rearrangement of Cyclic Ethynylcarbinol. I. Meyer-Schuster Rearrangement of Ethynylborneol.

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