Organophosphorus Compounds, Part 172; [1] The Formation of 1,3-1H-Diphospholes via Lithiumalkyl Adducts of 1,3,5-Triphosphabenzenes

Abstract

The organolithium adducts 2 and 3 of 1,3,5-triphosphabenzenes 1 release phosphinidene elements when heated. The resulting 1,3-diphospholide ions 4 react readily with primary alkyl halides with the formation of the 1,3-1H-diphospholes 5 and 6.

alkyl halides - diphospholes - heterocycles - organometallic reagents - phosphorus

References

<A NAME="RZ10803SS-1">1</A> Part 171: Steinbach J. Renner J. Binger P. Regitz M. Synthesis  2003,  1526 

<A NAME="RZ10803SS-2A">2a</A> Binger P. Leininger S. Stannek J. Gabor M. Mynott R. Bruckmann J. Krüger C. Angew. Chem., Int. Ed. Engl.  1995,  14:  2227 

<A NAME="RZ10803SS-2B">2b</A> Tabellion F. Nachbauer A. Leininger S. Peters C. Regitz M. Angew. Chem. Int. Ed.  1998,  37:  1233 

<A NAME="RZ10803SS-2C">2c</A> Heydt H. Topics Curr. Chem.  2003,  233:  216 

<A NAME="RZ10803SS-3">3</A> Cloke FGN. Hitchcock PB. Nixon JF. Wilson DJ. Organometallics  2000,  19:  219 

<A NAME="RZ10803SS-4">4</A> Stutzmann S. PhD Thesis   University of Kaiserslautern; Germany: 1997. 

<A NAME="RZ10803SS-5A">5a</A> Al-Juaid SS. Hitchcock PB. Matos RM. Nixon JF. J. Chem. Soc., Chem. Comm.  1993,  267 

<A NAME="RZ10803SS-5B">5b</A> Hitchcock PB. Matos RM. Nixon JF. J. Organomet. Chem.  1993,  462:  319 

<A NAME="RZ10803SS-5C">5c</A> Bartsch R. Hitchcock PB. Johnson JA. Matos RM. Nixon JF. Phosphorus, Sulfur Silicon Relat. Elem.  1993,  77:  45 

<A NAME="RZ10803SS-6">6</A> Stannek J. PhD Thesis   University of Kaiserslautern; Germany: 1996. 

<A NAME="RZ10803SS-7">7</A> Weidner S. PhD Thesis   University of Kaiserslautern; Germany: 2002. 

<A NAME="RZ10803SS-8A">8a</A> Issleib K. Leissring E. Meyer H. Tetrahedron Lett.  1981,  22:  4475 

<A NAME="RZ10803SS-8B">8b</A> Schmidt H. Leißring E. Issleib K. Z. Chem.  1988,  7:  255 

<A NAME="RZ10803SS-8C">8c</A> Issleib K. Schmidt H. Leissring E. J. Organomet. Chem.  1990,  382:  53 

<A NAME="RZ10803SS-9">9</A> Berger S. Braun S. Kalinowski H.-O. NMR-Spektroskopie von Nichtmetallen, ³¹ P NMR-Spektroskopie   Vol. 3:  Thieme; Stuttgart: 1991.  p.140 

<A NAME="RZ10803SS-10">10</A> Ecker A. Schmidt U. Chem. Ber.  1973,  106:  1453 

<A NAME="RZ10803SS-11A">11a</A>

Nixon J. F., personal communication

<A NAME="RZ10803SS-11B">11b</A> Clendenning SB. PhD Thesis   University of Sussex; UK, 2002. 

<A NAME="RZ10803SS-12A">12a</A> Ishmaeva EA. Patsanovskii JJ. Stepanova YZ. Becker G. Knoebel R. Weber U. Pudovic AN. Dokl. Akad. Nauk. SSSR  1986,  288:  160 

<A NAME="RZ10803SS-12B">12b</A> Tyler JK. J. Chem. Phys.  1964,  40:  1170