Hydrogen atom abstraction from hexamethyl(Dewar benzene), hexamethylprismane, and a 1,3-hydrogen-shifted isomer of hexamethylbenzvalene. A study by electron paramagnetic resonance spectroscopy

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DOIResolve DOI: http://doi.org/10.1021/jo00314a020
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TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
Volume46
Issue1
Pages9698; # of pages: 3
AbstractPhotochemically generated tert-butoxyls abstract an allylic hydrogen atom from hexamethyl(Dewar benzene). The resultant allylic radical [g = 2.00264, aH(2 H) = 12.40 G, aH(3 H) = 15.48 G] can be observed from 150 to 375 K. The same radical is formed by hydrogen abstraction from hexamethylprismane even at 140 K. In this case it is presumed to arise by two successive cyclopropylcarbinyl ring-opening rearrangements. Hydrogen abstraction from 1,2,4,5,6-pentamethyl-3-methylenetricyclo[3.1.0.02,6]hexane (the hexamethylbenzvalene isomer) also gave an allylic radical [g = 2.00259, aH(2 H) = 10.28 G, aH(3 H) = 16.98 G] which could be observed from 150 to 225 K. At higher temperatures this radical probably undergoes a rearrangement to a substituted cyclopropyl radical. The latter could not be detected, probably because of its high reactivity. © 1981 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276466
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Record identifier253776f3-9d99-4c23-b442-72dab506371f
Record created2015-10-13
Record modified2016-05-09
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