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Bimolecular Formation of Radicals by Hydrogen Transfer, 11. Transfer Hydrogenation of Conjugated Cyclic Dienes and Trienes

✍ Scribed by Morgenthaler, Jens ;Rüchardt, Christoph


Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
432 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

1,3‐Cyclohexadiene, 1,3‐cycloheptadiene and cycloheptatriene are smoothly hydrogenated to cyclohexene and cycloheptene, respectively, when heated to 260–340°C with an excess of 9,10‐dihydroanthracene (DHA) in diphenyl ether or benzonitrile. On the basis of a mechanistic study a nonchain three‐step mechanism is proposed which is initiated by a transfer of a hydrogen atom from DHA to the polyenes (retrodisproportionation).


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