Proton magnetic resonance of some 9,10-dihydroanthracenes
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 861-864
- https://doi.org/10.1039/j29660000861
Abstract
Reaction of dilithio- or disodio-anthracene with t-butyl chloride affords a mixture of 9-t-butyl- and 9,10-di-t-butyl-9,10-dihydroanthracene with some 1,4-di-t-butyl-1,4-dihydroanthracene. The nuclear magnetic resonance (n.m.r.) spectrum of the 9,10-di-t-butyl compound shows that it has either a planar conformation of the central ring or the trans configuration with rapid interconversion of the two conformers. Homo-allylic coupling is observed in the n.m.r. spectra of 9-t-butyl-9,10-dihydroanthracene and 1-phenyl-1,4-dihydronaphthalene, in the latter case with a coupling constant of 6 c./sec.Keywords
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