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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 6
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Original Articles

Two Simple Methods for the Synthesis of Trialkyl α-Aminophosphono-Acetates (3). Trifluoromethanesulfonyl Azide as an Azide-Transfer Agent

Gholam Hosein Hakimelahi Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, PQ, Canada, H3A 2K6
&
George Just Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, PQ, Canada, H3A 2K6
Pages 429-435 | Published online: 05 Dec 2006

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Roman Błaszczyk & Tadeusz Gajda. (2008) Convenient Synthesis of Dialkyl 1‐Azidoalkylphosphonates using Tetramethylguanidinium Azide as Azidation Agent. Synthetic Communications 38:7, pages 1110-1119.
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Tadeusz Gajda & Maciej Matusiak. (1992) An Efficient Synthesis of Diethyl 1-Aminoalkylphosphonate Hydrochlorides via the Intermediate Diethyl 1-Azidoalkylphosphonates. Synthetic Communications 22:15, pages 2193-2203.
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Articles from other publishers (32)

M.V. Krishna Rao, K. Nagarjuna Reddy, B. Sridhar & B.V. Subba Reddy. (2019) Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides. Tetrahedron Letters 60:41, pages 151083.
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Qing-Hai Deng, Tim Bleith, Hubert Wadepohl & Lutz H. Gade. (2013) Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles. Journal of the American Chemical Society 135:14, pages 5356-5359.
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Bagrat A. Shainyan & Ljudmila L. Tolstikova. (2012) Trifluoromethanesulfonamides and Related Compounds. Chemical Reviews 113:1, pages 699-733.
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Pieter P.J. Mortier, Frederik E.A. Van Waes, Kurt G.R. Masschelein, Thomas S.A. Heugebaert & Christian V. Stevens. (2011) Synthesis of N-vinyl 2,2-bisphosphonoaziridines from 1,1-bisphosphono-2-aza-1,3-dienes. Tetrahedron Letters 52:33, pages 4273-4276.
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Brian T. Chamberlain, Thomas G. Upton, Boris A. Kashemirov & Charles E. McKenna. (2011) α-Azido Bisphosphonates: Synthesis and Nucleotide Analogues. The Journal of Organic Chemistry 76:12, pages 5132-5136.
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Tamás Patonay, Krisztina Kónya & Éva Juhász-Tóth. (2011) Syntheses and transformations of α-azido ketones and related derivatives. Chemical Society Reviews 40:5, pages 2797.
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Sara Sobhani & Zahra Tashrifi. (2010) Synthesis of α-functionalized phosphonates from α-hydroxyphosphonates. Tetrahedron 66:7, pages 1429-1439.
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Dhurke Kashinath, Ghyslain Budin, Rachid Baati, St?phane Meunier & Alain Wagner. (2009) Azidation of ?-carbonyl lactones and lactams. Tetrahedron Letters 50:38, pages 5379-5381.
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Engelbert Ciganek. 2004. Organic Reactions. Organic Reactions 1 366 .
Paul A. Wender, Thomas E. Smith, Pierre Vogel & Sandrine Gerber-Lemaire. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Gholam Hossein Hakimelahi, Ali Akbar Moosavi-Movahedi, Ali Akbar Saboury, Valeriy Osetrov, Ghadam Ali Khodarahmi & Kak-Shan Shia. (2005) Carbapenem-based prodrugs. Design, synthesis, and biological evaluation of carbapenems. European Journal of Medicinal Chemistry 40:4, pages 339-349.
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Ender Erdik. (2004) Electrophilic α-amination of carbonyl compounds. Tetrahedron 60:40, pages 8747-8782.
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Habib Firouzabadi, Nasser Iranpoor & Sara Sobhani. (2004) PPh3/DDQ as a neutral system for the facile preparation of diethyl α-bromo, α-iodo and α-azidophosphonates from diethyl α-hydroxyphosphonates. Tetrahedron 60:1, pages 203-210.
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Philippe Savignac & Bogdan Iorga. 2003. Modern Phosphonate Chemistry. Modern Phosphonate Chemistry.
K. Krohn. 2003. Organic Synthesis Set. Organic Synthesis Set 45 53 .
Luisa Benati, Daniele Nanni & Piero Spagnolo. (1999) Reactions of Benzocyclic β-Keto Esters with Sulfonyl Azides. 2. 1 Further Insight into the Influence of Azide Structure and Solvent on the Reaction Course . The Journal of Organic Chemistry 64:14, pages 5132-5138.
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Leigh Ferris, David Haigh & Christopher J. Moody. (1996) N–H insertion reactions of rhodium carbenoids. Part 2. Preparation of N-substituted amino(phosphoryl)acetates (N-substituted phosphorylglycine esters). J. Chem. Soc., Perkin Trans. 1:24, pages 2885-2888.
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Masahiko Seki, Kazuhiko Kondo & Tameo Iwasaki. (1996) Novel approach to the synthesis of α-alkoxycarbonyl α-aminophosphonic esters based on a facile transformation of phosphoranes to phosphonic esters. J. Chem. Soc., Perkin Trans. 1:1, pages 3-5.
Crossref
. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1085 1229 .
Frances Heaney. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 451 504 .
J. Mulzer, H.‐J. Altenbach, M. Braun, K. Krohn & H.‐U. Reissig. 1990. Organic Synthesis Highlights. Organic Synthesis Highlights 45 53 .
Gholam H. Hakimelahi & Ali A. Jarrahpour. (2004) Synthesis of ethyl cis 2‐[(Diethoxyphosphoryl)methyl]‐7‐oxo‐3‐phenyl‐6‐phthalimido‐l‐azabicyclo[3.2.0]hept‐3‐ene‐2‐carboxylate and Methyl cis ‐2‐Bromo‐3‐methyl‐8‐oxo‐7‐phthalimido‐4‐oxa‐1‐azabicyclo[4.2.0]octane‐2‐carboxylate . Helvetica Chimica Acta 72:7, pages 1501-1505.
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Franz Baumberger, Andrea Vasella & Roland Schauer. (2004) Synthesis of New Sialidase Inhibitors, 6‐Amino‐6‐Deoxysialic Acids. Helvetica Chimica Acta 71:2, pages 429-445.
Crossref
. (2010) Elektrophile Aminierungen. Nachrichten aus Chemie, Technik und Laboratorium 35:10, pages 1047-1052.
Crossref
Alois Haas, Michael R. Chr. Gerstenberger & Dieter KoschelAlois Haas, Michael R. Chr. Gerstenberger & Dieter Koschel. 1987. F Perfluorohalogenoorgano Compounds of Main Group Elements. F Perfluorohalogenoorgano Compounds of Main Group Elements 1 252 .
Teruaki Mukaiyama, Hiroshi Suzuki & Tohru Yamada. (1986) THE DIASTEREOSELECTIVE ADDITION OF TIN(II) ENOLATES DERIVED FROM CARBOXYLIC THIOESTERS TO α-IMINOESTER. Chemistry Letters 15:6, pages 915-918.
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Yuan Cheng-Ye & Qi You-Mao. (1986) Studies on organophosphorus compounds: XV. A new method for the synthesis of α-amino-substituted benzylphosphonic acids. Acta Chimica Sinica 4:1, pages 93-100.
Crossref
Walter Lwowski. 1984. Azides and Nitrenes. Azides and Nitrenes 205 246 .
Gholam Hosein Hakimelahi. (2004) 132. The Synthesis of Highly Strained Monocyclic and Bicyclic β‐Lactams (Δ 1 ‐Carbapenem) . Helvetica Chimica Acta 65:5, pages 1378-1384.
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Gholam Hosein Hakimelahi & George Just. (2004) The Synthesis of 4‐Decarboxy‐4‐phosphono‐ O ‐2‐isooxacephems, ‐isopenams and ‐isooxacephems Containing Phosphorus at the 3‐Position . Helvetica Chimica Acta 65:5, pages 1359-1367.
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Ernest W. Colvin, Gordon W. Kirby & Arthur C. Wilson. (1982) (Diphenylphosphinyl)hydroxylamine: A new reagent for electrophilic -amination. Tetrahedron Letters 23:37, pages 3835-3836.
Crossref
G. H. HAKIMELAHI & G. JUST. (2016) ChemInform Abstract: TWO SIMPLE METHODS FOR THE SYNTHESIS OF TRIALKYL α‐AMINOPHOSPHONOACETATES. TRIFLUOROMETHANESULFONYL AZIDE AS AN AZIDE‐TRANSFER AGENT. Chemischer Informationsdienst 11:49.
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