Transannular Electronic Interactions between Nonconjugated Groups of 1, 6-Dimethylenecyclodecane and its Synthesis

South Carolina State College. Orangeburg, South Carolina

Manuscript received 12 September 1973; revised 21 June 1974; accepted 26 June 1974.

An interesting ten-membered medium-sized ring compound, 1, 6-dimethylenecyclodecane is synthesized, and its ultraviolet absorption spectrum in ethanol is studied. The compound exhibits an unusual absorption band at a wave-length of 256 nm, and has a molar extinction coefficient of 500 liter mole^-1 cm^-1. The origin of this transition and its assignment are discussed from the standpoint of the transannular double bond-double bond interaction. This is an interesting consequence of the stereochemistry of the ten-membered ring.