The orbital phase continuity-discontinuity property is shown to control electron delocalization and polarization even in open chain conjugated molecules. Its chemical consequences are discussed.

0.9 g of ZnCl2 was refluxed for 1 h, cooled, and treated with 10 mL of water, and 5.0 g of powdered K2Cr207 was added at once. This mixture was refluxed for 1 h, then cooled, and poured into ice and 20 mL of concentrated H2S04. After the usual workup and crystallization from benzene was obtained 4.1 g (90%) of yellow lib: mp 258-259 °C; m/e 335.979286, caled for CjgHgBrCb 335.978640.

Acyclic localization-delocalization of electrons in π-conjugated hydrocarbon polyions was predicted in terms of the continuity-discontinuity of the phase of the component orbitals. Many pairs of electron-localizing and -delocalizing conjugated polyions were designed as the model systems of which the relative stabilities have not been explored so far.

From the regioselectivity of deprotonation of 1,3-dimethyl-triptycene the LUMO of triptycene was concluded on some presently acceptable assumptions to be such e’ orbitals as expected from the significant contribution of the through-bond interaction.

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