Mono- and Bis-Carbonyl Hypoiodites of the Tertiary Amines Quinuclidine and DABCO

Abstract

Mono-and bis-carbonyl hypoiodites incorporating the tertiary amines quinuclidine (1a−e) or 1,4-diazabicyclo[2.2.2]octane (DABCO; 2a, 2b, and 2e), respectively, have been synthesized and represent the first examples of hypoiodites stabilized by alkyl amines rather than aromatic Lewis bases (e.g., pyridine derivatives). These highly reactive complexes have been characterized in the solid state by SCXRD and DFT calculations. The DABCO hypoiodite derivatives are rare examples of ditopic bis(O−I−N) complexes and were found to display unexpected bonding parameters relative to iodine(I) complexes in which the DABCO is coordinating in a monotopic manner.