Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2008(4): 586-588
DOI: 10.1055/s-2008-1042758
DOI: 10.1055/s-2008-1042758
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Benzylidenecyclopropanes from γ-Halopropyl Pentachlorophenyl Sulfones Using a Julia-Kocienski Olefination
Further Information
Received
16 November 2007
Publication Date:
12 February 2008 (online)
Publication History
Publication Date:
12 February 2008 (online)
Abstract
Simple, one-step synthesis of benzylidenecyclopropanes from γ-halopropyl pentachlorophenyl sulfones using a Julia-Kocienski olefination is reported.
Key words
Julia-Kocienski olefination - benzylidenecyclopropanes - sulfones - aldehydes
- Reviews:
-
1a
Brandi A.Goti A. Chem. Rev. 1998, 98: 589 -
1b
Brandi A.Cicchi S.Cordero FM.Goti A. Chem. Rev. 2003, 103: 1213 -
1c
Binger P.Buch HM. Top. Curr. Chem. 1987, 135: 77 -
2a
Stafford JA.McMurry JE. Tetrahedron Lett. 1998, 29: 2531 -
2b
Okuma K.Ikari K.Ono M.Sato Y.Kuge S.Ohta H.Machiguchi T. Bull. Chem. Soc. Jpn. 1995, 68: 2313 -
2c
Utimoto K.Tamura M.Sisido K. Tetrahedron 1973, 29: 1169 - 3
Cohen T.Sherbine JP.Matz JR.Hutchins RR.McHenry BM.Willey PR. J. Am. Chem. Soc. 1984, 106: 3245 - 4
Katritzky AR.Weihong D.Levell JR.Jianqing L. J. Org. Chem. 1998, 63: 6710 - For reviews on Julia-Kocienski olefination, see:
-
5a
Blakemore PR. J. Chem. Soc., Perkin Trans. 1 2002, 2563 -
5b
Plesniak K.Zarecki A.Wicha J. Curr. Chem. 2007, 275: 163 - For synthesis of alkenes by Julia-Kocienski olefination with using sulfones with electron-withdrawing group, see:
-
5c
Alonso DA.Fuensanta M.Najera C. Eur. J. Org. Chem. 2006, 4747 -
5d
Mirk D.Grassot J.-M.Zhu J. Synlett 2006, 1255 - 6
Bernard AM.Frongia A.Piras PP.Secci F. Synlett 2004, 1064 - 7
Fürstner A.Aissa C. J. Am. Chem. Soc. 2006, 128: 6306 -
8a
Mąkosza M.Judka M. Chem. Eur. J. 2002, 8: 4234 -
8b
Barbasiewicz M.Judka M.Mąkosza M. Russ. Chem. Bull. 2004, 53: 1846 - 9
Judka M. PhD Thesis Institute of Organic Chemistry PAS; Warsaw: 2004. -
11a
Mąkosza M.Judka M. Synlett 2004, 717 -
11b
M M.ąkosza Judka M. Helv. Chim. Acta 2005, 88: 1676 - 12
Nordvik T.Brinker UH. J. Org. Chem. 2003, 68: 7092 - 13
Salaun J.Hanack M. J. Org. Chem. 1975, 40: 1994
References and Notes
Pentachlorophenyl cyclopropyl sulfone was obtained from 3-bromopropyl pentachlorophenyl sulfone with 85% yield in the absence of carbonyl compounds.