Photochemical reactions of digermanyl-substituted naphthalenes: The germyl migration to the aromatic ring

Kunio Mochida, Hiroyuki Ginyama, Masae Takahashi, Mitsuo Kira

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Photochemical reactions of digermanyl-substituted naphthalenes have been investigated by chemical studies using trapping agents, laser flash photolysis, and ab initio MO calculations. Irradiation of 1-(pentamethyldigermanyl)naphthalene (1) afforded mainly an isomer, 1-(dimethylgermyl)-8-(trimethylgermyl)naphthalene (4), via photochemical formation of a pair of trimethylgermyl radical and 1- naphthyldimethylgermyl radical, and then recombination at the 8-position of the latter followed by an intramolecular 1,4-hydrogen shift. At the same time a small amount of 1-(trimethylgermyl)naphthalene (5) was formed through the dimethylgermylene extrusion from 1. From photolysis of 2-(pentamethyldigermany)naphthalene a high molecular weight polymer was obtained. The excited states of digermanyl-substituted naphthalenes responsible for the photodecomposition are also discussed.

Original languageEnglish
Pages (from-to)163-171
Number of pages9
JournalJournal of Organometallic Chemistry
Volume553
Issue number1-2
DOIs
Publication statusPublished - 1998 Feb 25
Externally publishedYes

Keywords

  • Germyl radical
  • Laser photolysis
  • Migration
  • Naphthylgermane
  • Photolysis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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