Studies in the Cycloproparene Series:1 An Experimental and Theoretical Investigation of Polar Dyes Derived from Cyclopropa[b]naphthalene.
1H-Cyclopropa[b]naphthalene is converted into novel polar olefins 15-19 via reaction of the 1,1-disilyl with anthrone-like ketones. The alkenes so formed are cryst., polar compds. that range in color from yellow to magenta. Solns. of the 10,10-dimethylanthrylidene 15, the xanthenylidene 16, and N-methylacrydinylidene 18 fluoresce; parent anthrone 19 likely phosphoresces. X-ray crystal structure detns. are reported for 15, 18, and the thioxanthenylidene 17. Theor. studies using ab initio calcns. at the HF/6-31G* level have been performed to provide assessments of the structures, charge distributions, and dipole moments of 15-19.
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