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- Institut für Organische Chemie (116) (remove)
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The transient [4+2]-cycloadducts from the title components eliminate nitrogen to form a 3,4-dihydro-2-pyrone derivative, a tricyclic cyclobutanone derivative and 2,5-dihydrooxepin-2-one derivatives, respectively.
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Carbon-13 shieldings and one-bond \(^{13}\)C-H coupling constants of bicydo[2.1.1]hexane, bicydo[2.l.l]hex- 2-ene, tricydo[3.1.1.0\(^{2.4}\)]heptane and benzvalene are presented and compared. to the data of related. compounds. H a bicydo[3.1.0]hexane system is part of a rigid skeleton, the cydopropane ring exerts spedfk: 'Y substituent eflects of two ldnds. In the case of the bicyclobexane boat form an upfield shift of the C-3 signal is observed and in tbe esse of the chair form a downfield shift of 15-20 ppm. Compared to the corresponding cydopentanes the double bond in strained cydopentenes causes downfield shifts of the C-4 absorption. 1bis eftect increases witb increasing strain, reaching 8 45.9 ppm maximum in benzvalene. Hence it is tbe only known bicydo[l.l.O]butane baving 8 reversed order of carbon shieldings. The downfield shifts are e:xplained by means of simple orbital interaction schemes.
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