(1) A reaction is termed stereospecific if starting materials differing only in their configuration are converted into stereoisomeric products. According to this definition, a stereospecific process is necessarily stereoselective but not all stereoselective processes are stereospecific. Stereospecificity may be total (100%) or partial. The term is also applied to situations where reaction can be performed with only one stereoisomer. For example the exclusive formation of trans-1,2-dibromocyclohexane upon bromination of cyclohexene is a stereospecific process, although the analogous reaction with (E)-cyclohexene has not been performed.

(2) The term has also been applied to describe a reaction of very high stereoselectivity, but this usage is unnecessary and is discouraged.

ELIEL (1962). [For the use of the term "stereospecific polymerization" see IUPAC POLYMERS (1981)]

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