Abstract
A variety of benzylic brominations were performed by using N -bromosuccinimide in (trifluoromethyl)benzene
with photochemical activation in the presence of 2,2′-azobisisobutyronitrile, 1,1′-azobis(cyclohexanecarbonitrile),
or benzoyl peroxide as the radical initiator. This system provides
clean, rapid, and high-yielding reactions with replacement of conventional
solvents, such as tetrachloromethane, by less-toxic (trifluoromethyl)benzene.
Key words
benzylic bromination - (trifluoromethyl)benzene - free radical -
N -bromosuccinimide - azobisisobutyronitrile
References
<A NAME="RP00609SS-1">1 </A>
Encyclopedia
of Reagents for Organic Synthesis
Vol. 1:
Paquette LA.
Wiley;
Chichester:
1995.
p.768-772
<A NAME="RP00609SS-2">2 </A>
Re-evaluation
of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide
1st
ed., Part II, Vol. 71:
IARC;
Lyon:
1999.
p.401-432
<A NAME="RP00609SS-3">3 </A>
Amijs CHM.
van Klink GPM.
van Koten G.
Green Chem.
2003,
5:
470
<A NAME="RP00609SS-4">4 </A>
Maul JJ.
Ostrowski PJ.
Ublacker GA.
Linclau B.
Curran DP.
Top. Curr. Chem.
1999,
206:
79
<A NAME="RP00609SS-5">5 </A>
Radleys Carousel from Radleys Discovery
Technologies; Shire Hill, Saffron Walden, Essex, CB11 3AZ, UK
<A NAME="RP00609SS-6">6 </A>
The Merck Index. An Encyclopedia
of Chemicals and Drugs
12th ed:
Budavari S.
Merck;
Whitehouse Station
NJ:
1996.
p.Entry 1142
<A NAME="RP00609SS-7">7 </A>
Offermann W.
Vögtle F.
Angew. Chem., Int.
Ed. Engl.
1980,
19:
464 ; Angew. Chem. 1980 , 92 , 471
<A NAME="RP00609SS-8">8 </A>
Fernandez R.
PhD
Thesis
University of Newcastle upon Tyne;
UK:
2002.
<A NAME="RP00609SS-9">9 </A>
Sket B.
Zupan M.
J. Org. Chem.
1986,
51:
929
<A NAME="RP00609SS-10">10 </A>
Makhija MT.
Kasliwal RT.
Kulkarni VM.
Neamati N.
Bioorg.
Med. Chem.
2004,
12:
2317
<A NAME="RP00609SS-11">11 </A>
Togo H.
Hirai T.
Synlett
2003,
702
<A NAME="RP00609SS-12">12 </A>
Waykole L.
Prashad M.
Palermo S.
Repic O.
Blacklock TJ.
Synth.
Commun.
1997,
27:
2159
<A NAME="RP00609SS-13">13 </A>
Offermann W.
Vögtle F.
Synthesis
1977,
272
<A NAME="RP00609SS-14">14 </A>
Hou CJ.
Okamoto Y.
J. Org. Chem.
1982,
47:
1977
<A NAME="RP00609SS-15">15 </A>
Deshpande AM.
Natu AA.
Argade NP.
J.
Org. Chem.
1998,
63:
9557
<A NAME="RP00609SS-16">16 </A>
Podgoršek A.
Stavber S.
Zupan M.
Iskra J.
Tetrahedron Lett.
2006,
47:
7245
<A NAME="RP00609SS-17">17 </A>
Shaw H.
Perlmutter HD.
Gu C.
Arco SD.
Quibuyen TO.
J. Org. Chem.
1997,
62:
236
<A NAME="RP00609SS-18">18 </A>
Cash MT.
Schreiner PR.
Phillips RS.
Org. Biomol. Chem.
2005,
3:
3701
