RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(2): 259-266
DOI: 10.1055/s-0029-1217103
DOI: 10.1055/s-0029-1217103
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Diethyl [Nitro(diazo)methyl]phosphonate: Synthesis and Reactivity towards Alkenes
Weitere Informationen
Received
4 September 2009
Publikationsdatum:
06. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
06. November 2009 (online)
Abstract
A novel and convenient synthesis of diethyl [nitro(diazo)methyl]phosphonate and its reactions with various alkenes are described. The reactivity of diethyl [nitro(diazo)methyl]phosphonate is shown to be dependent on the structure of the alkene. A number of cyclopropyl α-nitrophosphonates were obtained.
Key words
diazo compounds - phosphonates - alkenes - cyclopropanation - carbenes
- 1
Sheridan RP. J. Chem. Inf. Comput. Sci. 2002, 42: 103 - For comprehensive reviews, see:
-
2a
Ordóñez M.Rojas-Cabrera H.Cativiela C. Tetrahedron 2009, 65: 17 -
2b
Kafarski B.Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193 -
2c
Wolfenden R. Annu. Rev. Biophys. Bioeng. 1976, 5: 271 - 3 For a recent review, see:
Brackmann F.de Meijere A. Chem. Rev. 2007, 107: 4493 -
4a
Erion MD.Walsh CT. Biochemistry 1987, 26: 3417 -
4b
Groth U.Lehmann L.Richter L.Schöllkopf U. Liebigs Ann. Chem. 1993, 427 -
4c
Yamazaki S.Takada T.Moriguchi Y.Yamabe S. J. Org. Chem. 1998, 63: 5919 -
4d
Fadel A. J. Org. Chem. 1999, 64: 4953 -
4e
Tesson N.Dorigneux B.Fadel A. Tetrahedron: Asymmetry 2002, 13: 2267 -
5a
Yashin NV.Averina EB.Gerdov SM.Kuznetsova TS.Zefirov NS. Tetrahedron Lett. 2003, 44: 8241 -
5b
Yashin NV.Averina EB.Grishin YuK.Kuznetsova TS.Zefirov NS. Synthesis 2006, 279 -
6a
Averina EB.Yashin NV.Kuznetsova TS.Zefirov NS. Vestn. Mosk. Univer., Ser. 2: Khim. 2002, 43: 246 ; Chem. Abstr. 2002, 138, 254854 -
6b
Averina EB.Yashin NV.Shvorina EB.Grishin YuK.Kuznetsova TS. Vestn. Mosk. Univer., Ser. 2: Khim. 2005, 46: 314 ; Chem. Abstr. 2005, 145, 145989 -
6c
Yashin NV.Averina EB.Grishin YuK.Kuznetsova TS.Zefirov NS. Synthesis 2006, 880 -
7a
Matveeva ED.Podrugina TA.Tishkovskaja EV.Tomilova LG.Zefirov NS. Synlett 2003, 2321 -
7b
Zefirov NS.Matveeva ED. ARKIVOC 2008, (i): 1 -
7c
Yashin NV.Villemson EV.Chemagin AV.Averina EB.Kabachnik MM.Kuznetsova TS. Synthesis 2008, 464 - 8
Regitz M.Weber B.Eckstein U. Liebigs Ann. Chem. 1979, 1002 -
9a
Sifniades S. J. Org. Chem. 1975, 40: 3562 -
9b
Neimysheva AA.Muratov SS.Smirnov EV.Solntseva LM. Zh. Obshch. Khim. 1976, 46: 940 ; Chem. Abstr. 1976, 85, 712 -
9c
Takeuchi Y.Ogura H.Kanada A.Koizumi T. J. Org. Chem. 1992, 57: 2196 - 10
Charette AB.Wurz RP.Ollevier T. J. Org. Chem. 2000, 65: 9252 -
11a
Charette AB.Wurz RP. J. Mol. Catal. A: Chem. 2003, 196: 83 -
11b
Titanyuk ID.Beletskaya IP.Peregudov AS.Osipov SN. J. Fluorine Chem. 2007, 128: 723 - 12
Charette AB.Wurz RP.Ollevier T. Helv. Chim. Acta 2002, 85: 4468 - 13
Perrin DD.Armarego WLF. Purification of Laboratory Chemicals Pergamon; Oxford: 1966. p.362 - 14
Calogeropoulou T.Hammond GB.Wiemer DF. J. Org. Chem. 1987, 52: 4185 - 15
Binger P.Brinkmann A.Wedemann P. Synthesis 2002, 1344 - 16
Zefirov NS.Kozhushkov SI.Kuznetsova TS.Kokoreva OV.Lukin KA.Trach SS.Ugrak BI. J. Am. Chem. Soc. 1990, 112: 7702 - 17
Sternberg E.Binger P. Tetrahedron Lett. 1985, 26: 301 - 18
Cripps HN.Williams JK.Sharkey WH. J. Am. Chem. Soc. 1959, 81: 2723 - 19
Beckhaus H.-D.Ruechardt C.Kozhushkov SI.Belov VN.Verevkin SP.de Meijere A. J. Am. Chem. Soc. 1995, 117: 11854 - 20
Christol H.Cristau H.-J.Soleiman M. Synthesis 1975, 736 - 21
Neimysheva AA.Muratov SS.Smirnov EV.Solntseva LM. Zh. Obshch. Khim. 1976, 46: 940 ; Chem. Abstr. 1976, 85, 712