Summary.
Reaction of triphenylphosphine and an electron deficient acetylenic ester in the presence of strong N–H acid such as alkyl and aryl sulfamides or acetamide produces phosphorous ylides at room temperature in CH2Cl2. The aryl sulfamide phosphoranes undergo a smooth transformation reaction in boiling toluene and produce iminophosphoranes.
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References
a) Arques A, Molina P (2004) Curr Org Chem 8: 827; b) Fresneda PM, Molina P (2004) Synlett 1; c) Steiner A, Zacchini S, Richards PI (2002) Coord Chem Rev 227: 193; and references therein
a) Hoesl CE, Nefzi A, Houghten RA (2003) J Comb Chem 5: 155; b) Johnson AW, Kaska WC, Starzewski KAO, Dixon DA “Ylides and Imines of Phosphorus” Wiley: New York, 1993; Chapter 13 and references therein
a) Staudinger H, Meyer J (1919) Helv Chim Acta 2: 635; b) Staudinger H, Hauser E (1921) Helv Chim Acta 4: 861; c) Shaw RA, Fitzsimmons BW, Smith BC (1962) Chem Rev 62: 247; d) Eric FVS, Kenneth T (1988) Chem Rev 88: 297
AV Kirsanov RG Makitra (1956) Zh Obshch Khim 26 907 Occurrence Handle1:CAS:528:DyaG28XnslKrtw%3D%3D
a) Eguchi S, Okawa T, “In Recent Res Devel Org Chem Transworld Research Network, Trivandrum”; Pandalai SG Ed, Wiley, 1997; Vol 1, pp 337; b) Molina P, Vilaplana MJ (1994) Synthesis 1197
a) Eguchi S, Matsushita Y, Yamashita K (1992) Org Prep Proceed Int 24: 209; b) Wamhoff H, Richardt G, Stolben S (1995) Advances in Heterocyclic Chemistry. In: Katritzky AL (ed) Academic: Orlando (FL), vol 64, pp 159; c) Gussar NI (1991) Russ Chem Rev 60: 146
a) Saito T, Satsumabayashi S (1998) J Chem Soc, Perkin Trans 1, 986; b) Okawa T, Eguchi S (1998) Tetrahedron 54: 5853
a) Molina P, Fresneda PM, Delgado S (1999) Synthesis 326; b) Takahashi M, Suga D (1998) Synthesis 986; c) Shi C, Zhang Q, Wang KK (1999) J Org Chem 64: 925; d) Gololov Y, Zhmurova IN, Kasukhin LF (1981) Tetrahedron 37: 437
Hudson HR (1990) The Chemistry of Organophosphorus Compounds: Primary Secondary and Tertiary Phosphinesand Heterocyclic Organophosphorus(III) Compounds. In: Hantely FR (ed) Wiley: New York, pp 386–472
R Engel (1998) “Synthesis of Carbon-Phosphorus Bonds” CRC Press Boca Raton, FL
JIG Cadogan (1979) “Organophosphorus Reagents in Organic Synthesis” Academic Press New York
BE Maryanoff AB Reitz (1989) Chem Rev 89 863 Occurrence Handle10.1021/cr00094a007 Occurrence Handle1:CAS:528:DyaL1MXktVKmsb4%3D
OI Kolodiazhynyi (1997) Russ Chem Rev 66 225 Occurrence Handle10.1070/RC1997v066n03ABEH000232
AJ Arduago CA Stewart (1994) Chem Rev 94 1215 Occurrence Handle10.1021/cr00029a003
KM Pietrusiewiz M Zabloka (1994) Chem Rev 94 1375 Occurrence Handle10.1021/cr00029a009
HJ Bestmann O Vostrowsky (1983) Top Curr Chem 109 85 Occurrence Handle1:CAS:528:DyaL3sXltVGjs7k%3D Occurrence Handle10.1007/BFb0018057
MV George SK Khetan RK Gupta (1976) Adv Heterocycl Chem 19 354
R Burgada Y Leroux YUE Khoshnieh (1981) Tetrahedron Lett 22 3533 Occurrence Handle10.1016/S0040-4039(01)81950-X Occurrence Handle1:CAS:528:DyaL38Xlt1eqsw%3D%3D
a) Shaabani A, Teimouri MB, Yavari I, Norouzi-Arasi H, Bijanzadeh HR (2000) J Fluorine Chem 103: 155; b) Shaabani A, Safaei HR, Bijanzadeh HR (2001) Synth Commun 31: 2639
a) Shaabani A, Safaei HR, Hemyari K, Moghimi A (2001) J Chem Res (s) 192; b) Shaabani A, Bazgir A, Teimouri MB, Bijanzadeh HR (2002) Phosphorus Sulfur and Silicon 177: 833; c) Shaabani A, Teimouri MB, Bijanzadeh HR (2004) Russ J Org Chem 40: 976
I Yavari N Zabarjad-Shiraz (2001) Phosphorus Sulfur and Silicon 176 141 Occurrence Handle1:CAS:528:DC%2BD38XivFKrtA%3D%3D
I Yavari N Zabarjad-Shiraz HR Bijanzadeh (2004) Phosphorus Sulfur and Silicon 179 1381 Occurrence Handle10.1080/10426500490463556 Occurrence Handle1:CAS:528:DC%2BD2cXltFGhsL8%3D
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Shaabani, A., Rahmati, A. & Naderi, S. An Easy One-Pot Procedure for the Synthesis of N-Sulfonyl Phosphorous Ylides and Sulfonyl Iminophosphoranes. Monatsh. Chem. 138, 553–557 (2007). https://doi.org/10.1007/s00706-007-0640-3
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DOI: https://doi.org/10.1007/s00706-007-0640-3