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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.


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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.