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Evidence for a synfacial nucleophilic displacement with allylic rearrangement. Mechanistic conclusions. Preliminary communication
Author(s) -
Jefford C. W.,
Sweeney A.,
Hill D. T.,
Delay F.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540621
Subject(s) - chemistry , allylic rearrangement , nucleophile , reagent , lithium aluminium hydride , halide , hydride , bromide , lithium (medication) , medicinal chemistry , aluminum hydride , photochemistry , stereochemistry , inorganic chemistry , organic chemistry , ion , catalysis , medicine , hydrogen , methoxide , endocrinology
Reduction of exo ‐2‐methyl‐3, 4‐dichlorobicyclo[3.2.1]oct‐2‐ene and the exo ‐2‐phenyl‐3,4‐dibromo analogue with lithium aluminium hydride proceeds mainly with allylic rearrangement. Moreover, hydride enters and bromide leaves synfacially. The stereochemistry of the process is discussed in the light of the favourable energy of a quasi‐cyclic transition state in which reagent and halide are complexed.