TY - JOUR
T1 - Synthesis, Characterization, and Chemistry of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes
T2 - Reactions at Neopentyl Sites
AU - Kumar, Kanta
AU - Wang, Shin
AU - Sukenik, Chaim N.
PY - 1984/7
Y1 - 1984/7
N2 - This paper reports the synthesis and characterization of a series of 15 new, symmetric, 1,4-disubstituted bicyclo[2.2.2]octyl derivatives. Beyond detailing their syntheses and spectral properties, it describes the scope of synthetic transformations that can be effected at these neopentyl-like centers. The question of a possible direct displacement by hydride at such a site, as per an earlier literature report, is considered, and the limits of this and related substitution reactions are delineated. The scope of reactions at sp2centers attached to these positions is also defined.
AB - This paper reports the synthesis and characterization of a series of 15 new, symmetric, 1,4-disubstituted bicyclo[2.2.2]octyl derivatives. Beyond detailing their syntheses and spectral properties, it describes the scope of synthetic transformations that can be effected at these neopentyl-like centers. The question of a possible direct displacement by hydride at such a site, as per an earlier literature report, is considered, and the limits of this and related substitution reactions are delineated. The scope of reactions at sp2centers attached to these positions is also defined.
UR - http://www.scopus.com/inward/record.url?scp=4444253015&partnerID=8YFLogxK
U2 - 10.1021/jo00178a018
DO - 10.1021/jo00178a018
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AN - SCOPUS:4444253015
SN - 0022-3263
VL - 49
SP - 665
EP - 670
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -