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

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 degrees C), and the resultant C-H and O-H insertion products were analyzed semi-quantitatively by LC/ESl-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. (C) 2008 Elsevier Ltd. All rights reserved.