Cl3CCONH2/PPh3
2855
pp. 40–44; (e) Pearson, A. J.; Roush, W. R. (Eds.). Handbook of Reagents for
Organic Synthesis: Activating Agents and Protecting Groups; Wiley:
New York, 1999; pp. 333, 335–338, and 370–373.
5. Morrison, R. T.; Boyd, R. N. Organic Chemistry, 7th ed.; Prentice-Hall
International: Englewood Cliffs, N. J., 1999; pp. 760–762.
6. (a) Lee, J. B. Preparation of acid chlorides under very mild conditions. J. Am.
Chem. Soc. 1966, 88, 3440–3441; (b) Barstow, L. E.; Hruby, V. J. A simple
method for the synthesis of amides. J. Org. Chem. 1971, 36, 1305–1306; (c)
Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G.
Preparation of alkyl chlorides, acid chlorides, and amides using polymer-
supported phosphines and carbon tetrachloride: Mechanism of these reac-
tions. J. Org. Chem. 1983, 48, 3721–3728.
7. Venkataraman, K.; Wagle, D. R. Cyanuric chloride: A useful reagent
for converting carboxylic acids into chlorides, esters, amides and peptides.
Tetrahedron Lett. 1979, 32, 3037–3040.
8. Devos, A.; Remion, J.; Frisque-Hesbain, A. M.; Colens, A.; Ghosez, L.
Synthesis of acyl halides under very mild conditions. J. Chem. Soc., Chem.
Commun. 1979, 24, 1180–1181.
9. Villeneuve G. B.; Chan, T. H. A rapid, mild, and acid-free procedure for the
preparation of acyl chorides including formyl chloride. Tetrahedron Lett.
1997, 38, 6489–6492.
10. Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F. Facile conversion of
alcohols into their bromides and iodides by N-bromo and N-iodosaccharins=
triphenylphosphine under neutral conditions. Tetrahedron Lett. 2006, 47,
1771–1775.
11. Rodrigues, R. C. C.; Barros, I. M. A.; Lima, E. L. S. Mild one-pot conver-
sion of carboxylic acids to amides or esters with Ph3P=trichloroisocyanuric
acid. Tetrahedron Lett. 2005, 46, 5945–5947.
12. Kang, D. H.; Joo, T. Y.; Lee, E. H.; Chaysripongkul, S.; Chavasiri, W.;
Jang, D. O. A mild and efficient reaction for conversion of carboxylic acids
into acid bromides with ethyl tribromoacetate=triphenylphosphine under
acid-free conditions. Tetrahedron Lett. 2006, 47, 5693–5696.
13. Jang, D. O.; Park, D. J.; Kim, J. A mild and efficient procedure for the
preparation of acid chlorides from carboxylic acids. Tetrahedron Lett.
1999, 40, 5323–5326; (b) Jang, D. O.; Cho, D. H.; Kim, J.-G. One-pot prep-
aration of esters from carboxylic acids using the PPh3-CCl3CN system. Synth.
Commun. 2003, 33, 2885–2890; (c) Kim, J.; Jang, D. O. A convenient method
for synthesis of symmetrical acid anhydrides from carboxylic acids with
trichloroacetronitrile and triphenylphosphine. Synth. Commun. 2001, 31,
395–399.
14. Chantarasriwong, O.; Jang, D. O.; Chavasiri, W. A practical and efficient
method for the preparation of sulfonamides utilizing Cl3CCN=PPh3. Tetra-
hedron Lett. 2006, 47, 7489–7492.
15. Haveux, B.; Dekoker, A.; Rens, M.; Sidani, A. R.; Toye, J.; Ghosez, L.
a-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N, N,
2-trimethylpropenylamine. Org. Syn. Coll. 1988, 6, 282.