Main > A1. CORP. INDEX. Rn-Rz > Rutgers State University of NJ/P > 2005. 10.03.2005. (CCl2 Route)

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New route to dichlorocarbene
The reactive intermediate dichlorocarbene (CCl2) can be photolytically generated from a number of precursors, but these procedures also generate aromatic by-products that can interfere with spectroscopic studies. Now, chemists at Rutgers University in New Brunswick, N.J., have found a way to prepare a nitrogenous precursor to CCl2, opening the way for detailed spectroscopic study of this carbene. The new precursor is dichlorodiazirine (shown). It was synthesized by treating 3-p-nitrophenoxy-3-chlorodiazirine with excess chloride ion, resulting in substitution of the p-nitrophenoxy group by chloride. Dichlorodiazirine is moderately stable at 25 °C in the dark and can be photolyzed cleanly to CCl2 and N2. “This preparation ends a 40-year search for a spectroscopically user-friendly precursor for CCl2,” says professor Robert A. Moss, who reports the findings with coworkers Gaosheng Chu and Ronald R. Sauers (J. Am. Chem. Soc. 2005, 127, 14206). “Since the article was submitted,” Moss adds, “we have obtained the first solution UV spectrum of this archetypal carbene.”




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