Medium-Sized Cyclophanes. III. The Nitration Reaction of [2.2]Metacyclophane with Benzoyl Nitrate
- 1 March 1967
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 40 (3) , 600-605
- https://doi.org/10.1246/bcsj.40.600
Abstract
The nitration reaction of [2.2]metacyclophane was carried out using dilute nitric acid or benzoyl nitrate under various conditions. Dilute nitric acid afforded 2-nitro-4, 5, 9, 10-tetrahydro-pyrene as the sole product, confirming Allinger’s original experiments, whereas benzoyl nitrate furnished a complex mixture consisting of 4, 5, 9, 10-tetrahydropyrene, 4, 5-dihydropyrene and pyrene, together with the nitration product. A series of experiments established that 4, 5, 9, 10-tetrahydropyrene, which was formed by the 1, 4-elimination reaction of Allinger’s intermediate, was the initial product of the reaction. Two competitive reactions, nitration and dehydrogenation reactions of the tetrahydropyrene, were assumed to be occurring, thus accounting for the experimental results.This publication has 13 references indexed in Scilit:
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