Diethyl [Nitro(diazo)methyl]phosphonate: Synthesis and reactivity towards alkenes

Synthesis

Volumn , Issue 2, 2010, Pages 259-266

  Chemagin, Andrey V ^a   Yashin, Nikolai V ^a,b   Grishin, Yuri K ^a   Kuznetsova, Tamara S ^a,b   Zefirov, Nikolai S ^a,b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

Author keywords

Alkenes; Carbenes; Cyclopropanation; Diazo compounds; Phosphonates

Indexed keywords

CARBENES; CYCLOPROPANATION; CYCLOPROPYL; DIAZO COMPOUNDS; PHOSPHONATES;

COMPLEXATION;

OLEFINS;

ALKENE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOPROPANATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 73949104111     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217103     Document Type: Article

References (21)

1. Sheridan R P., J. Chem. Inf. Comput. Sci. 2002 42 103
2. For comprehensive reviews, see:, Ordóñez M, Rojas-Cabrera H, Cativiela C, Tetrahedron 2009 65 17, Kafarski B, Lejczak B, Phosphorus, Sulfur Silicon Relat. Elem. 1991 63 193, Wolfenden R, Annu. Rev. Biophys. Bioeng. 1976 5 271
3. For a recent review, see:, Brackmann F, deMeijere A, Chem. Rev. 2007 107 4493
4. Erion M D., Walsh C T., Biochemistry 1987 26 3417, Groth U, Lehmann L, Richter L, Schöllkopf U, Liebigs Ann. Chem. 1993 427, Yamazaki S, Takada T, Moriguchi Y, Yamabe S, J. Org. Chem. 1998 63 5919, Fadel A, J. Org. Chem. 1999 64 4953, Tesson N, Dorigneux B, Fadel A, Tetrahedron: Asymmetry 2002 13 2267
5. Yashin N V., Averina E B., Gerdov S M., Kuznetsova T S., Zefirov N S., Tetrahedron Lett. 2003 44 8241, Yashin N V., Averina E B., Grishin Yu K., Kuznetsova T S., Zefirov N S., Synthesis 2006 279
6. Averina E B., Yashin N V., Kuznetsova T S., Zefirov N S., Vestn. Mosk. Univer., Ser. 2: Khim. 2002 43 246; Chem. Abstr. 2002, 138, 254854, Averina E B., Yashin N V., Shvorina E B., Grishin Yu K., Kuznetsova T S., Vestn. Mosk. Univer., Ser. 2: Khim. 2005 46 314; Chem. Abstr. 2005, 145, 145989, Yashin N V., Averina E B., Grishin Yu K., Kuznetsova T S., Zefirov N S., Synthesis 2006 880
7. Matveeva E D., Podrugina T A., Tishkovskaja E V., Tomilova L G., Zefirov N S., Synlett 2003 2321, Zefirov N S., Matveeva E D., ARKIVOC 2008 (i) 1, Yashin N V., Villemson E V., Chemagin A V., Averina E B., Kabachnik M M., Kuznetsova T S., Synthesis 2008 464
8. Regitz M, Weber B, Eckstein U, Liebigs Ann. Chem. 1979 1002
9. Sifniades S, J. Org. Chem. 1975 40 3562, Neimysheva A A., Muratov S S., Smirnov E V., Solntseva L M., Zh. Obshch. Khim. 1976 46 940; Chem. Abstr. 1976, 85, 712, Takeuchi Y, Ogura H, Kanada A, Koizumi T, J. Org. Chem. 1992 57 2196
10. Charette A B., Wurz R P., Ollevier T, J. Org. Chem. 2000 65 9252
11. Charette A B., Wurz R P., J. Mol. Catal. A: Chem. 2003 196 83, Titanyuk I D., Beletskaya I P., Peregudov A S., Osipov S N., J. Fluorine Chem. 2007 128 723
12. Charette A B., Wurz R P., Ollevier T, Helv. Chim. Acta 2002 85 4468
13. Perrin D D., Armarego W L. F., Purification of Laboratory Chemicals Pergamon Oxford 1966 362
14. Calogeropoulou T, Hammond G B., Wiemer D F., J. Org. Chem. 1987 52 4185
15. Binger P, Brinkmann A, Wedemann P, Synthesis 2002 1344
16. Zefirov N S., Kozhushkov S I., Kuznetsova T S., Kokoreva O V., Lukin K A., Trach S S., Ugrak B I., J.Am. Chem. Soc. 1990 112 7702
17. Sternberg E, Binger P, Tetrahedron Lett. 1985 26 301
18. Cripps H N., Williams J K., Sharkey W H., J. Am. Chem. Soc. 1959 81 2723
19. Beckhaus H.-D, Ruechardt C, Kozhushkov S I., Belov V N., Verevkin S P., deMeijere A, J. Am. Chem. Soc. 1995 117 11854
20. Christol H, Cristau H.-J, Soleiman M, Synthesis 1975 736
21. Neimysheva A A., Muratov S S., Smirnov E V., Solntseva L M., Zh. Obshch. Khim. 1976 46 940; Chem. Abstr. 1976, 85, 712