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- see also Clayden , J. , ed. 2002 . “ By comparison, a sulfinyl substituent also causes extensive epimerization from the ortho-position at the benzylic carbon of the epoxide, whereas meta- and para-sulfinyl-substituted styrene oxides undergo exclusive hydrogen/lithium exchange ortho to the sulfinyl group when treated with LDA/THF, with the epoxide stereochemistry remaining unaffected (see Ref. 3). This is in line with the fact that sulfoxides, in contrast with sulfides, are, indeed, more powerful directed ortho metalation groups by virtue of better coordination and acidifying effects ” . In Organolithium: Selectivity for Synthesis , 47 Amsterdam : Pergamon . However, while in the case of the sulfenyl-substituted styrene oxide, the epoxide successfully strives with such a functional group to bind the lithium thus facilitating benzylic deprotonation (complex-induced proximity effect, see Ref. 1b), a similar competition with the epoxide ring does not occur with sulfinyl derivatives
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