TY - JOUR
T1 - Distribution of photo-cross-linked products from 3-aryl-3-trifluoromethyldiazirines and alcohols
AU - Kanoh, Naoki
AU - Nakamura, Takemichi
AU - Honda, Kaori
AU - Yamakoshi, Hiroyuki
AU - Iwabuchi, Yoshiharu
AU - Osada, Hiroyuki
N1 - Funding Information:
The authors thank Ms. A. Asami for her technical support. This work was supported in part by the Daiichi Pharmaceutical Award in Synthetic Organic Chemistry; the Chemical Biology Project of RIKEN; grants from the MEXT, Japan; and a Grant-in-Aid for Scientific Research (C) (No. 17510187) from JSPS, Japan.
PY - 2008/6/9
Y1 - 2008/6/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=43149121993&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=43149121993&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.04.031
DO - 10.1016/j.tet.2008.04.031
M3 - Article
AN - SCOPUS:43149121993
SN - 0040-4020
VL - 64
SP - 5692
EP - 5698
JO - Tetrahedron
JF - Tetrahedron
IS - 24
ER -