The Reactions of 3,6-Di-tert-butyl-1,2-benzoquinone and 3,6-Ditert-butylcatechol with tert-Butyl Hydroperoxide. -The reaction of the title quinone (I) as well as its corresponding catechol with tert-butyl hydroperoxide in aprotic solvents results in ring oxidation accompanied by ring expansion furn
Cycloaddition reactions of cyclooctyne with 9,10-phenanthrenequinone and 3,5-di-tert-butyl-o-benzoquinone
✍ Scribed by W. Verboom; H. J. T. Bos
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 606 KB
- Volume
- 100
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
Treatment of a solution of 9,10‐phenanthrenequinone 4 and cyclooctyne 2 in chloroform with boron trifluoride‐ether affords the quinoid α,β‐unsaturated ketone 5 with loss of carbon monoxide. Reaction of 3,5‐di‐tert‐butyl‐o‐benzoquinone 9 with cyclooctyne 2 gives rise to formation of the Diels‐Alder adduct 10 and a bridged cycloheptadienone derivative 11; under the influence of boron trifluoride‐ether, however, the reaction leads, in addition to 11, to formation of the isomeric cycloheptadienone derivative 12, while the Diels‐Alder adduct 10 is converted into the cycloheptadienone derivative 11.
📜 SIMILAR VOLUMES
## Abstract The reduction of 3,6‐di‐__tert__‐butyl‐__o__‐benzoquinone with tin amalgam gives the different tin catecholate complexes. The use of polar solvents for this reaction leads to the formation of Cat~2~Sn · L~2~ species (where Cat—dianion of 3,6‐di‐__tert__‐butylcatechol, L = Et~2~O, THF, P
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