peri-Interaction between diarylmethyl and diarylmethylium units in 1,8-disubstituted naphthalenes: Preference of localized structure for the C-H bridged carbocation

Hidetoshi Kawai, Takayuki Nagasu, Takashi Takeda, Kenshu Fujiwara, Takashi Tsuji, Masakazu Ohkita, Jun Ichi Nishida, Takanori Suzuki

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

(8-Diarylmethyl-1-naphthyl)bis(4-dimethylaminophenyl)methyliums (aryl=C6H5, 4-IC6H4, and 4-MeOC 6H4) were generated by hydride shift from (4-dimethylaminophenyl)methyl group to the diarylmethylium unit at peri-positions of naphthalene. Successful isolation and low-temperature X-ray analysis indicated that they are novel C-H bridged carbocations, which prefer the localized structure with a short contact of C-H⋯C+ rather than the delocalized one with a three-centered-two-electron bond of (C⋯H⋯C)+.

Original languageEnglish
Pages (from-to)4553-4558
Number of pages6
JournalTetrahedron Letters
Volume45
Issue number23
DOIs
Publication statusPublished - 2004 May 31
Externally publishedYes

Keywords

  • Carbocation
  • Hydride shift
  • Three-centered-two-electron bond
  • Triarylmethylium
  • peri-Interaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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