Transannular Electronic Interaction of 1, 6-Cyclodecanedithione and Its Synthesis

South Carolina State College Orangeburg, South Carolina 29117

Manuscript received 24 May 1976, accepted 18 November 1977

An interesting ten-membered medium-sized ring compound, 1, 6-cyclodecanedithione, is prepared and its ultraviolet absorption spectra in carbon tetrachloride, tetrahydrofuran and chloroform are studied. The compound exhibits and unusual absorption bands at the wavelengths of 265 nm, 275 mu and 310 nm and have the molar absorptivities of 2657, 890 and 640 liter mole^-1 cm^-1 in carbon tetrachloride, tetrahydrofuran and chloroform respectively. The presence of a strong absorption band at 265 nm region is taken an evidence for this transannular electronic interaction in the excited state. The origin of π→π* transition (K-band) and its assignment are discussed from the standpoint of the transannular electronic interaction (Transannular Conjugation)¹. This is an interesting consequence of the stereochemistry of the ten-membered ring.