Organic Chemistry

How to bring two chlorines face to face

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Science  06 Feb 2015:
Vol. 347, Issue 6222, pp. 624
DOI: 10.1126/science.347.6222.624-b

Organic chemists have known for well over a century how to chlorinate the carbons at both ends of a double bond. A vast array of different methods now exists to replace the chlorines with other molecular fragments. One persistent limitation, however, has been the tendency of the two chlorines to bond to opposite faces of the starting compound. Cresswell et al. now present a versatile method that adds both chlorines to the same face. The key is a selenium catalyst that probably binds to the face opposite the first chlorine, before being displaced from behind by the second.

Nat. Chem. 10.1038/nchem.2141 (2015).

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