Semipinacol and protoadamantane-adamantane rearrangements of 5, 6-dibromoadamantan-2-one and -2-ol. Issue 20 (18th May 2017)

• Record Type: Journal Article
• Authors: Wang, Xiaofang; Dong, Yuxiang; Ezell, Edward L.; Garrison, Jered C.; Wood, James K.; Hagen, James P.; Vennerstrom, Jonathan L.
• Is Part Of: Tetrahedron. Volume 73:Issue 20(2017)
• Page Start: 2972
• Page End: 2976
• Publication Date: 2017-05-18
• Subjects: Semipinacol rearrangement -- Protoadamantane-adamantane rearrangement -- Polybrominated adamantanes -- 1, 2, 6-Trisubstituted adamantanes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.04.006
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: