Microwave irradiation in organophosphorus chemistry. Part 2: Synthesis of phosphonium salts

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1339-1341

  Kiddle, James J ^a  

^a UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

Author keywords

Microwave heating; Phosphonium salts; Wittig reaction; Ylide

Indexed keywords

ORGANOHALOGEN DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHOSPHONIUM DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HEATING; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034716559     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02288-1     Document Type: Article

References (15)

1. For Part 1, see: Kiddle, J. J.; Gurley, A. F. Phosphorus, Sulfur Silicon Relat. Elem. 1999, accepted.
2. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
3. Lawrence, N. J. In Preparation of Alkenes, a Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: London, 1996; pp. 19-58, and references cited therein.
4. (a) Gedye, R.; Smith, F.; Westaway, K.; Humera, A.; Baldisera, L.; Laberge, L.; Roussel, J. Tetrahedron Lett. 1986, 27, 279-282.
5. (b) Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948.
6. For reviews, see: (a) Majetich, G.; Wheless, K. In Microwave-Enhanced Chemistry Fundamentals, Sample Preparation, and Applications; Kingston, H. M.; Haswell, S. J., Eds.; American Chemical Society: Washington DC, 1997, pp. 455-505.
7. (b) Caddick, S. Tetrahedron 1995, 51, 10 403-10432.
8. (a) Xu, C. D.; Chen, G. Y.; Huang, X. Chinese Chem. Lett. 1995, 6, 467-468.
9. (b) Xu, C. D.; Chen, G. Y.; Huang, X. Org. Prep. Proc. 1995, 27, 559-561.
10. (c) Xu, C. D.; Chen, G. Y.; Huang, X. Synth. Commun. 1995, 25, 2229-2233.
11. (d) Spinella, A.; Fortuanti, T.; Soriente, A. Synlett 1997, 93-94.
12. Caution! It is hazardous to rapidly heat organic reactions in closed vessels by either traditional means or with microwave irradiation. Therefore, caution should be exercised when conducting reactions of this type. A typical procedure for the synthesis of the phosphonium salts follows: Organic halide (1 equiv.) and triphenylphosphine (1 equiv.) are added either neat or in 5 ml of xylene to a pressure tube with a threaded Teflon cap (Ace Glass). The threaded cap on the pressure tube is sealed finger tight, and the tube placed in a beaker surrounded by glass wool. The glass wool not only serves to evenly heat the tube, but to absorb the reaction mixture if the tube were to shatter. The tube and beaker are then placed in the microwave oven (Panasonic) and heated for the appropriate time on high power (1100 watts). Once the heating cycle is complete and the beaker and tube have cooled to ambient temperature, the tube is opened and the phosphonium salts are removed and purified by recrystallization from an appropriate solvent.
13. 31P NMR data consistent with those previously reported. See Ref. 3 and those sited therein.
14. Albright, T. A.; Freeman, W. J.; Schweizer, E. E. J. Am. Chem. Soc. 1975, 97, 2946-2950. Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem. 1966, 31, 334-33
15. Albright, T. A.; Freeman, W. J.; Schweizer, E. E. J. Am. Chem. Soc. 1975, 97, 2946-2950. Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem. 1966, 31, 334-336.