Reactive Organic Intermediates from Diazirines

New Synthesis of the DihalodiazirinesNew syntheses of the dihalodiazirines permit Professor Robert A. Moss and his group to generate dihalocarbenes by laser flash photolysis (LFP) and to study the fundamental kinetic and energetic properties of highly reactive species that survive for less than milliseconds.

The dihalocarbenes (dichlorocarbene, CCl2, chlorofluorocarbene, CClF, and difluorocarbene, CF2) are representative of synthetically important, highly reactive, and very short-lived reaction intermediates. We have studied the complexation of CCl2 with aryl ethers, the formation of trihalomethide carbanions by reaction of CCl2 with chloride or bromide, and determined the activation energies for the additions of the carbenes to olefins.


Publication: 

"Directly Observed Halocarbene - Halocarbanion Equilibration," L. Wang, R.A. Moss, and K. Krogh-Jespersen, J. Am. Chem. Soc., 134, 17459 (2012).

"Evolution of Structure and Reactivity in a Series of Iconic Carbenes" (Featured Article), M. Zhang, R.A. Moss, J. Thompson, and K. Krogh-Jespersen, J. Org. Chem., 77, 843 (2012).

Group Members: 

Dr. Lei Wang, Dr. Pablo Hoijemberg

Year of Research Highlight: 
2012