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.

Key words

alkyl halides - diphospholes - heterocycles - organometallic reagents - phosphorus

References

• 1 Part 171: Steinbach J. Renner J. Binger P. Regitz M. Synthesis  2003,  1526 
• 2a Binger P. Leininger S. Stannek J. Gabor M. Mynott R. Bruckmann J. Krüger C. Angew. Chem., Int. Ed. Engl.  1995,  14:  2227 
• 2b Tabellion F. Nachbauer A. Leininger S. Peters C. Regitz M. Angew. Chem. Int. Ed.  1998,  37:  1233 
• 2c Heydt H. Topics Curr. Chem.  2003,  233:  216 
• 3 Cloke FGN. Hitchcock PB. Nixon JF. Wilson DJ. Organometallics  2000,  19:  219 
• 4 Stutzmann S. PhD Thesis   University of Kaiserslautern; Germany: 1997. 
• 5a Al-Juaid SS. Hitchcock PB. Matos RM. Nixon JF. J. Chem. Soc., Chem. Comm.  1993,  267 
• 5b Hitchcock PB. Matos RM. Nixon JF. J. Organomet. Chem.  1993,  462:  319 
• 5c Bartsch R. Hitchcock PB. Johnson JA. Matos RM. Nixon JF. Phosphorus, Sulfur Silicon Relat. Elem.  1993,  77:  45 
• 6 Stannek J. PhD Thesis   University of Kaiserslautern; Germany: 1996. 
• 7 Weidner S. PhD Thesis   University of Kaiserslautern; Germany: 2002. 
• 8a Issleib K. Leissring E. Meyer H. Tetrahedron Lett.  1981,  22:  4475 
• 8b Schmidt H. Leißring E. Issleib K. Z. Chem.  1988,  7:  255 
• 8c Issleib K. Schmidt H. Leissring E. J. Organomet. Chem.  1990,  382:  53 
• 9 Berger S. Braun S. Kalinowski H.-O. NMR-Spektroskopie von Nichtmetallen, ³¹ P NMR-Spektroskopie   Vol. 3:  Thieme; Stuttgart: 1991.  p.140 
• 10 Ecker A. Schmidt U. Chem. Ber.  1973,  106:  1453 
• 11a

  Nixon J. F., personal communication

• 11b Clendenning SB. PhD Thesis   University of Sussex; UK, 2002. 
• 12a Ishmaeva EA. Patsanovskii JJ. Stepanova YZ. Becker G. Knoebel R. Weber U. Pudovic AN. Dokl. Akad. Nauk. SSSR  1986,  288:  160 
• 12b Tyler JK. J. Chem. Phys.  1964,  40:  1170