Abstract
The reaction of dibenzofuran or dinaphthofuran with lithium in anhydrous diethyl ether
led to a solution of the corresponding C,O-dilithiated intermediate which, upon treatment
with 1,3,3-trimethylindolin-2-one or different coumarin derivatives at -78 °C, afforded,
after hydrolysis, dibenzospiropyrans and dinaphthospiropyrans in good yields. The
structures of all new compounds were determined by single crystal X-ray analysis.
Key words
dibenzofuran - dibenzospiropyran - dinaphthofuran - dinaphthospiropyran - reductive
ring opening
References
<A NAME="RF05007SS-1">1 </A>
Crano JC.
Guglielmetti RJ.
Organic Photochromic and Thermochromic Compounds
Plenum Press;
New York:
1999.
<A NAME="RF05007SS-2">2 </A>
Guo X.
Zhang D.
Tao H.
Zhu D.
Org. Lett.
2004,
6:
2491
<A NAME="RF05007SS-3">3 </A>
Kado S.
Yamada K.
Murakami T.
Kimura K.
J. Am. Chem. Soc.
2005,
127:
3030
<A NAME="RF05007SS-4">4 </A>
Zhu L.
Zhu M.
Kurst JK.
Li ADQ.
J. Am. Chem. Soc.
2005,
127:
8968
<A NAME="RF05007SS-5">5 </A>
Sakata T.
Yan Y.
Marriott G.
J. Org. Chem.
2005,
70:
2009
<A NAME="RF05007SS-6">6 </A>
Zhou Y.
Zhang D.
Zhang Y.
Tang Y.
Zhu D.
J. Org. Chem.
2005,
70:
6164
<A NAME="RF05007SS-7">7 </A>
Lu NT.
Nguyen VN.
Kumar S.
McCurdy A.
J. Org. Chem.
2005,
70:
9067
<A NAME="RF05007SS-8">8 </A>
Wang B.
Li M.
Xu S.
Song H.
Wang B.
J. Org. Chem.
2006,
71:
8291
<A NAME="RF05007SS-9">9 </A>
Wang B.
Li M.
Xu S.
Song H.
Wang B.
Synthesis
2007,
1304
<A NAME="RF05007SS-10">10 </A>
Gilman H.
Esmay DL.
J. Am. Chem. Soc.
1953,
75:
2947
<A NAME="RF05007SS-11">11 </A>
Kadyrou R.
Heinicke J.
Kinderman MK.
Heller D.
Fischer C.
Selke R.
Fischer AK.
Jones PG.
Chem. Ber.
1997,
130:
1663
<A NAME="RF05007SS-12">12 </A>
Luo Y.
Wang F.
Zhu G.
Zhang Z.
Tetrahedron: Asymmetry
2004,
15:
17
<A NAME="RF05007SS-13">13 </A>
Xie X.
Zhang TY.
Zhang Z.
J. Org. Chem.
2006,
71:
6522
<A NAME="RF05007SS-14">14 </A>
Langer P.
Freiberg W.
Chem. Rev.
2004,
104:
4125
<A NAME="RF05007SS-15">15 </A>
Crystallographic data for the structures in this paper have been deposited with the
Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 638816-638825
for compounds 3 -6 . Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union
Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
<A NAME="RF05007SS-16">16 </A>
Beyersbergen van Henegouwen WG.
Fieseler RM.
Rutjes FPJT.
Hiemstra H.
J. Org. Chem.
2000,
65:
8317
<A NAME="RF05007SS-17">17 </A>
Koepp E.
Vögtle F.
Synthesis
1987,
177