[3+2] Cycloaddition of Diazocarbonyl Compounds to 1,1-Dinitroethenes: Synthesis of Functionalized gem-Dinitrocyclopropanes

Olga A. Ivanova; Ekaterina M. Budynina; Elena B. Averina; Tamara S. Kuznetsova; Yurii K. Grishin; Nikolai S. Zefirov

doi:10.1055/s-2007-983727

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-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2007(13): 2009-2013
DOI: 10.1055/s-2007-983727

PAPER

[3+2] Cycloaddition of Diazocarbonyl Compounds to 1,1-Dinitroethenes: Synthesis of Functionalized gem-Dinitrocyclopropanes

Olga A. Ivanova^a,b, Ekaterina M. Budynina^a, Elena B. Averina^a, Tamara S. Kuznetsova*^a,b, Yurii K. Grishin^a, Nikolai S. Zefirov^a,b
^a Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119992, Russian Federation
Fax: +7(495)9390290;
^b IPhaC RAS, Severnyi Proezd 1, Chernogolovka, Moscow Region 142432, Russian Federation
e-Mail: kuzn@org.chem.msu.ru;

Further Information

Publication History

Received 7 March 2007
Publication Date:
18 June 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The synthesis of functionalized gem-dinitrocyclopropanes via [3+2] cycloaddition of diazocarbonyl compounds with 1,1-dinitroethenes [in some cases in the presence of Mo(CO)₆ as catalyst] has been developed.

Key words

[3+2] cycloaddition - α-diazocarbonyl compound - 1,1-dinitroethene - 1,1-dinitrocyclopropane - hexacarbonylmolybdenum

References

1a Wade PA. Daily WP. Carroll PJ. J. Am. Chem. Soc. 1987, 109: 5452

Crossref Google Scholar
1b Agrawal JP. Hodgson RD. In Organic Chemistry of Explosives Wiley; Chichester: 2007. p.68-69

Crossref Google Scholar
2a Ivanova OA. Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Izv. Akad. Nauk, Ser. Khim. 2001, 11: 2008 ; Russ. Chem. Bull. 2001, 50, 2101

Article in Thieme Connect Google Scholar
2b Budynina EM. Averina EB. Ivanova OA. Yashin NV. Kuznetsova TS. Zefirov NS. Synthesis 2004, 2609

Article in Thieme Connect Google Scholar
3a Maas G. In Houben-Weyl Vol. E17a: de Meijere A. Thieme; Stuttgart: 1997. p.426-435

Google Scholar
3b Shapiro EA. Dyadkin AB. Nefedov OM. Diazoesters Nauka; Moscow: 1992. p.29-30 ; (in Russian)

Google Scholar
4a Wulfman DS. Linstrumelle G. Cooper CF. In The Chemistry of the Diazonium and Diazo Groups Part 2: Patai S. Wiley; New York: 1978. p.821

Google Scholar
4b Machezie K. In The Chemistry of the Hydrazo, Azo and Azoxy Groups Part 1: Patai S. Wiley; New York: 1975. p.239

Google Scholar
5a Engel PS. Chem. Rev. 1980, 80: 99

Google Scholar
5b Ye T. McKervey MA. Chem. Rev. 1994, 94: 1143

Google Scholar
6 Regitz M. Heydt H. In 1,3-Dipolar Cycloaddition Chemistry Vol. 1: Padwa A. Wiley; New York: 1984. p.393

Google Scholar
7 Fridman AL. Gabitov FA. Surkov VD. Zh. Org. Khim. 1972, 8: 2457 ; Chem. Abstr. 1973, 78, 83543

Google Scholar
8a Duden P. Pondorff W. Ber. Dtsch. Chem. Ges. 1905, 38: 2031

Crossref Google Scholar
8b Gold MH. Hamel EE. Klager K. J. Org. Chem. 1957, 22: 1665

Crossref Google Scholar
9 Novikov SS. Belikov VM. Dem’yanenko VF. Lapshina LV. Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk 1960, 7: 1295 ; Chem. Abstr. 1961, 55, 423d

Google Scholar
10 Grakauskas V. Guest AM. J. Org. Chem. 1978, 43: 3485

Crossref Google Scholar
11a Doyle MP. Davidson JG. J. Org. Chem. 1980, 45: 1538

Crossref Google Scholar
11b Doyle MP. Dorow RL. Tamblyn WH. J. Org. Chem. 1982, 47: 4059

Crossref Google Scholar
11c Doyle MP. Colsman MR. Dorow RL. Heterocycl. Chem. 1983, 20: 943

Crossref Google Scholar
12 Tomilov YuV. Platonov DN. Averkiev BB. Shulishov EV. Nefedov OM. Izv. Akad. Nauk, Ser. Khim. 2003, 1: 176 ; Russ. Chem. Bull. 2003, 52, 187-191

Google Scholar
13a Contreras RH. Peralta JE. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 37: 321

Crossref Google Scholar
13b Watt VS. Goldstein JH. Chem. Phys. 1967, 46: 4165

Crossref Google Scholar
13c Crecely LM. Watt VS. Goldstein JH. J. Mol. Spectrosc. 1969, 30: 184

Crossref Google Scholar
14 Newman MS. Ottmann GF. Grundmann CF. Org. Synth. Coll. Vol. IV John Wiley & Sons; London: 1963. p.424

Google Scholar
15 Jung E. Min S.-J. Houk KN. Ess D. J. Org. Chem. 2004, 69: 9085

Crossref Google Scholar
16 Regitz M. Menz F. Chem. Ber. 1968, 101: 2622

Crossref Google Scholar
17 Barrett AGM. Braddock DC. Lenoir I. Tone H. J. Org. Chem. 2001, 66: 8260

Crossref Google Scholar
18 Wenkert E. Alonso ME. Buckwalter BL. Chou KJ. J. Am. Chem. Soc. 1977, 99: 4778

Crossref Google Scholar