Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol

Xiaofang Wang, Yuxiang Dong, Edward L. Ezell, Jered C Garrison, James K. Wood, James P. Hagen, Jonathan L Vennerstrom

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)2972-2976
Number of pages5
JournalTetrahedron
Volume73
Issue number20
DOIs
StatePublished - Jan 1 2017

Fingerprint

Adamantane
Halogenation
semipinacol

Keywords

  • 1,2,6-Trisubstituted adamantanes
  • Polybrominated adamantanes
  • Protoadamantane-adamantane rearrangement
  • Semipinacol rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol. / Wang, Xiaofang; Dong, Yuxiang; Ezell, Edward L.; Garrison, Jered C; Wood, James K.; Hagen, James P.; Vennerstrom, Jonathan L.

In: Tetrahedron, Vol. 73, No. 20, 01.01.2017, p. 2972-2976.

Research output: Contribution to journalArticle

@article{e43a77377ce44409a5cb20a27e364ede,
title = "Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol",
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.",
keywords = "1,2,6-Trisubstituted adamantanes, Polybrominated adamantanes, Protoadamantane-adamantane rearrangement, Semipinacol rearrangement",
author = "Xiaofang Wang and Yuxiang Dong and Ezell, {Edward L.} and Garrison, {Jered C} and Wood, {James K.} and Hagen, {James P.} and Vennerstrom, {Jonathan L}",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.tet.2017.04.006",
language = "English (US)",
volume = "73",
pages = "2972--2976",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "20",

}

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

PY - 2017/1/1

Y1 - 2017/1/1

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

UR - http://www.scopus.com/inward/record.url?scp=85017172544&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85017172544&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.04.006

DO - 10.1016/j.tet.2017.04.006

M3 - Article

AN - SCOPUS:85017172544

VL - 73

SP - 2972

EP - 2976

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -