Distribution of photo-cross-linked products from 3-aryl-3-trifluoromethyldiazirines and alcohols

Naoki Kanoh, Takemichi Nakamura, Kaori Honda, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Hiroyuki Osada

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The photolysis of N-[4-(3-trifluoromethyl-3H-diazirin-3-yl)benzoyl]-2,2′-ethylenedioxybis(ethylamine) (1) in EtOH, PrOH, i-PrOH, BuOH, and i-BuOH was carried out in both solution (at room temperature) and solid phase (at -196 °C), and the resultant C-H and O-H insertion products were analyzed semi-quantitatively by LC/ESI-MS/MS. The carbene insertion reactions at low temperature produced all possible C-H and O-H insertion products in a relatively uniform distribution, which could not be accomplished by the solution-phase reaction.

Original languageEnglish
Pages (from-to)5692-5698
Number of pages7
JournalTetrahedron
Volume64
Issue number24
DOIs
Publication statusPublished - 2008 Jun 9

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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