α-Haloenamines as Reagents for the Conversion of Phosphorus Oxyacids to Their Halogenated Analogues

Rikard Norlin; Lars Juhlin; Per Lind; Lars Trogen

doi:10.1055/s-2005-865363

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 2005(11): 1765-1770
DOI: 10.1055/s-2005-865363

PAPER

α-Haloenamines as Reagents for the Conversion of Phosphorus Oxyacids to Their Halogenated Analogues

Rikard Norlin*, Lars Juhlin, Per Lind, Lars Trogen
Swedish Defence Research Agency, Division of NBC-Defence, Department of Threat Assessment, Cementvägen 20, 90182 Umeå, Sweden
Fax: +46(90)106809; e-Mail: rikard.norlin@foi.se;

Further Information

Publication History

Received 12 January 2005
Publication Date:
02 May 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Phosphorus oxyacids are converted to their halogenated analogues under mild conditions. α-Haloenamines are shown to be effective halogen transfer reagents affording good to high yields of the desired products at reaction times, in some cases, less than one minute.

Key words

phosphorus - α-haloenamines - halogenation - fluorine - chlorine

References

1 Ferguson CG. Gorin BI. Thatcher GRJ. J. Org. Chem. 2000, 65: 1218

Crossref Google Scholar
2 Allcock HR. Hofmann MA. Wood RM. Macromolecules 2001, 34: 6915

Crossref Google Scholar
3 Nivsarkar M. Gupta AK. Kaushik MP. Tetrahedron Lett. 2004, 45: 6863

Crossref Google Scholar
4 Nawrot B. Sobczak M. Antoszczyk S. Org. Lett. 2002, 4: 1799

Crossref Google Scholar
5a Munyemana F. Frisque-Hesbain AM. Devos A. Ghosez L. Tetrahedron Lett. 1989, 30: 3077

Crossref Google Scholar
5b Singh A. Markowitz M. Tsao LI. Synth. Commun. 1992, 22: 2293

Crossref Google Scholar
6 Devos A. Remion J. Frisque-Hesbain AM. Colens A. Ghosez L. J. Chem. Soc., Chem. Commun. 1979, 1180

Crossref Google Scholar
7a Schmidt U. Kroner M. Beutler U. Synthesis 1988, 475

Google Scholar
7b Fujisawa T. Mori T. Higuchi K. Sato T. Chem. Lett. 1983, 1791

Google Scholar
8 Petrov KA. Baksova RA. Khorkhoyanu LV. Libman BY. Sinogeikina LP. Zh. Prikl. Khim. 1966, 39: 2798

Google Scholar
9 Schmidt U. Lieberknecht A. Griesser H. Utz R. Beutler T. Bartkowiak F. Synthesis 1986, 361

Article in Thieme Connect Google Scholar
10 Ernst B. Winkler T. Tetrahedron Lett. 1989, 30: 3081

Crossref Google Scholar
11 Colens A. Demuylder M. Téchy B. Ghosez L. Nouv. J. Chim. 1977, 1: 369

Google Scholar
12 Colens A. Ghosez L. Nouv. J. Chim. 1977, 1: 371

Google Scholar
13 Chai J. Wathey B. Tetrahedron Lett. 2001, 42: 1383

Crossref Google Scholar
14 Ghosez L. George-Koch I. Patiny L. Houtekie M. Bovy P. Nshimyumukiza P. Phan T. Tetrahedron 1998, 54: 9207

Crossref Google Scholar
15 Bendall JG. Payne AN. Screen TEO. Holmes AB. Chem. Commun. 1997, 1067

Crossref Google Scholar
16 Seel F. Vellerman K.-D. Chem. Ber. 1971, 104: 2972

Crossref Google Scholar
17 Moedritzer K. Millier RE. Synth. React. Inorg. Met.-Org. Chem. 1974, 4: 417

Google Scholar
18 Abduvakhabov AA. Sadykov AA. Zuparova KM. Aslanov KA. Sadykov AS. Dokl. Akad. Nauk Uzb. SSR 1973, 30: 41

Google Scholar
19 Michalski J. Mlotkowska M. Skowronska A. J. Chem. Soc., Perkin Trans. 1 1974, 319

Crossref Google Scholar
20 Horner L. Gehring R. Phosphorus, Sulfur Relat. Elem. 1981, 11: 157

Google Scholar
21 Nixon JF. Schmutzler R. Spectrochim. Acta 1964, 20: 1835

Crossref Google Scholar
22 Fokin AV. Landau MA. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 2435 ; Izv. Akad. Nauk SSSR, Ser. Khim. (Engl. Transl.), 1976, 2271

Google Scholar
23 Miao Z. Li H. Zhou Y. Feng R. Li G. Junshi Yixue Kexueyuan Yuankan 1999, 23: 205

Google Scholar
24 Nikitin EV. Parakin OV. Romanov GV. Ignatev YA. Romakhin AS. Kargin YM. Pudovik AN. Dokl. Akad. Nauk SSSR, Ser. Khim. 1980, 252: 922 ; Dokl. Akad. Nauk SSSR, Ser. Khim. (Engl. Transl.) 1980, 442

Google Scholar