Ag. Martinez et al., Chemoselective reaction of spiro[oxirane-2,2 '-norborn]-1 '-yl triflates with nucleophiles: a new case of HSAB-principle dependence, TETRAHEDR L, 42(47), 2001, pp. 8293-8296
The preparation of two new spiro[oxirane-2,2'-norborn]-1'-yl triflates as w
ell as the study on the behavior of such triflates under nucleophile treatm
ent is reported. Three different nucleophile reagents have been chosen for
this study: aqueous ethanol (a weak hard-base nucleophile), sodium hydroxid
e (a strong hard-base nucleophile) and lithium aluminum hydride (a strong s
oft-base nucleophile). It is concluded that the described norbornane-derive
d bridgehead triflates react chemo selectively with these nucleophiles foll
owing one of three possible reaction pathways, according to the character (
strong or weak nucleophile, hard or soft base) of the reagent. For strong n
ucleophiles the HSAB principle is fulfilled. (C) 2001 Elsevier Science Ltd.
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