Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures

Haruo Aikawa, Yusuke Takahira, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Single enantiomers of 1,8-di(1-adamantyl)naphthalenes were synthesized by the [4+2]cycloaddition reaction of 6-adamantylbenzyne and 2-adamantylfuran. The enantiomers were resolved by conversion into diastereomeric ketopinic acid esters. The absolute configuration was determined by X-ray analysis. Kinetic studies by CD revealed an enantiomerization barrier of 29 kcal mol−1 for 1,8-(1-adamantyl)naphthalenes.

Original languageEnglish
Pages (from-to)1479-1481
Number of pages3
JournalChemical Communications
Volume47
Issue number5
DOIs
Publication statusPublished - 2011 Feb 7

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures'. Together they form a unique fingerprint.

Cite this