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Theoretical Investigation of the Mechanism of the Baeyer-Villiger Reaction in Nonpolar Solvents

✍ Scribed by Dr. Yoshishige Okuno


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
940 KB
Volume
3
Category
Article
ISSN
0947-6539

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✦ Synopsis


The reaction of hexakis(di-and 1 6 % yields, respectively. 'H and 13C the symmetric unti-all-trans isomer 3b is broniomethy1)benzene with [(Bu,P),-N M R spectroscopy suggest that 3 is obnot obtained at all. The X-ray structures Ni(COD)] (COD = 1,5-cyclooctadiene) tained as the .sjwall-rrun,s isomer 3a, and of 3a and 4 arc reported. The hexaradi- in DMF at 65-70 'C yielded a mixture of alene 4 has a chair conformation, and dethe title compounds. The mixture was sepby column chromatography to yield hexabromotricyclobutabenzene (3 a) and hexabromohexaradialene (4) in 24 viates from planarity by 43.6'. Heat or radical impurities cause the clean transformation of 3a to 4. Keywords crystal structure . cyclobutenes . nickel . radialenes . radical reactions .~ Instilut fur Anorganischc Cheinic der Universitit Universititsstrasse 5-7. 11-481 17 Essen (Germany) Fax. Int. code +(2011183-2535 mediated cyclization method (Scheme I),['*] in the hope that the efficiency of the reaction in closing one four-membered ring , . e-mail: boese(ir structchem uni-esscn de would permit the cyclization of three rings within the same 208 ___ I<, VCH l~~r/ir~s,~esel/schu// mhH, D-694Si W&/wim, 1997


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