TY - JOUR
T1 - Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol
AU - Wang, Xiaofang
AU - Dong, Yuxiang
AU - Ezell, Edward L.
AU - Garrison, Jered C.
AU - Wood, James K.
AU - Hagen, James P.
AU - Vennerstrom, Jonathan L.
N1 - Funding Information:
We thank the Medicines for Malaria Venture (MMV) for generous support of this research. We acknowledge the NIH (P30CA036727) and the Nebraska Research Initiative for their support of the Eppley Structural Biology NMR Facility.
Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2017
Y1 - 2017
N2 - A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes.
AB - A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes.
KW - 1,2,6-Trisubstituted adamantanes
KW - Polybrominated adamantanes
KW - Protoadamantane-adamantane rearrangement
KW - Semipinacol rearrangement
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U2 - 10.1016/j.tet.2017.04.006
DO - 10.1016/j.tet.2017.04.006
M3 - Article
AN - SCOPUS:85017172544
SN - 0040-4020
VL - 73
SP - 2972
EP - 2976
JO - Tetrahedron
JF - Tetrahedron
IS - 20
ER -