34029-54-4Relevant academic research and scientific papers
Electrophilic Substitution in Annulenes. Part 4. Transmission of Substituent Effects in 1,6-Methanoannulene, determined via Protiodesilylation: Evidence for Substantial C(1)-C(6) Transannular Orbital Interaction
Suzuki, Tsuyoshi,Takase, Kahei,Takahashi, Kazuko,Laws, Andrew P.,Taylor, Roger
, p. 697 - 700 (1988)
The rates of acid-catalysed desilylation of a series of 7-substituted 2-trimethylsilyl-1,6-methanoannulenes have been measured spectrophotometrically at 50 degC using a mixture of aqueous perchloric acid and methanol (2:5 v/v).The substituent effects
Applications of MCD Spectroscopy: MO Ordering and Transannular Interaction in 1,6-Methanoannulenes from Analysis of Substituent Effects
Klingensmith, Kenneth A.,Puettmann, Wilhelm,Vogel, Emanuel,Michi, Josef
, p. 3375 - 3380 (2007/10/02)
Eight 2-substituted and nine 3-substituted 1,6-methanoannulenes have been synthesized, and their magnetic circular dichroism has been measured.The B terms of the Lb transition depend on the ?-electron effect of the substituent in a way which reveals the ordering of the four frontier molecular orbitals: a1, a2, b1, and b2 in the order of increasing energy.This result implies the presence of a strong transannular interaction between the bridgehead positions 1 and 6 on the bridged annulene ring.
