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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 5
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Original Articles

One-Step Conversion of Aldehydes to Nitriles. Introduction of a One-Carbon Unit

Albert M. van Leusen Department of Organic Chemistry, The University Nijenborgh, Groningen, The Netherlands
&
Piet G. Oomkes Department of Organic Chemistry, The University Nijenborgh, Groningen, The Netherlands
Pages 399-403 | Published online: 05 Dec 2006

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Ahmed A. Fadda, Nesma M. Bayoumy & Khaled M. Elattar. (2015) Recent Progress in the Chemistry of 2-Tosylacetonitrile. Synthetic Communications 45:23, pages 2637-2675.
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VishnuK. Tandon & Sanjay Rai. (2003) p-Toluenesulfonylmethyl Isocyanide: A Versatile Synthon in Organic Chemistry. Sulfur reports 24:3, pages 307-385.
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J.Y. Merour & A. Buzas. (1988) A Convenient Synthesis of Tryptamines. Synthetic Communications 18:18, pages 2331-2335.
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Shinya Harusawa, Shuji Nakamura, Sayoko Yagi, Takushi Kurihara, Yasumasa Hamada & Takayuki Shioiri. (1984) A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents via Cyanophosphates1). Synthetic Communications 14:14, pages 1365-1371.
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O. H. Oldenziel, J. Wildeman & A. M. van Leusen. 2003. Organic Syntheses. Organic Syntheses 8 8 .
A Tsotinis, M Panoussopoulou, K Hough & D Sugden. (2003) Synthesis and biological evaluation of new β,β′-disubstituted 6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl ethylamido melatoninergic ligands. European Journal of Pharmaceutical Sciences 18:5, pages 297-304.
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Thomas A. Engler, Kelly Furness, Sushant Malhotra, Clive Diefenbacher & Joshua R. Clayton. (2003) An improved method for direct conversion of heteroaryl-aldehydes to heteroaryl-acetonitriles. Tetrahedron Letters 44:14, pages 2903-2905.
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Daan Van Leusen & Albert M. Van Leusen. 2004. Organic Reactions. Organic Reactions 417 666 .
Albert M. van Leusen & Daan van Leusen. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Robert Aslanian, Joan E. Brown, N.-Y. Shih, Mwangi wa Mutahi, Michael J. Green, Susan She, Maurice Del Prado, Robert West & John Hey. (1998) 4- [(1H - imidazol - 4 - YL) methyl] benzamidines and benzylamidines: novel antagonists of the histamine H3 receptor. Bioorganic & Medicinal Chemistry Letters 8:16, pages 2263-2268.
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Clemens Lamberth. (1998) p-Tolysulfonylmethyl Isocyanide (TosMIC) - a versatile formaldehyde equivalent with reversed polarity. Journal f�r Praktische Chemie/Chemiker-Zeitung 340:5, pages 483-485.
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Gonzalo Blay, Luz Cardona, Begoña García, Luisa Lahoz & JoséR. Pedro. (1996) The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride. Tetrahedron 52:25, pages 8611-8618.
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. 1993. Sulphones in Organic Synthesis. Sulphones in Organic Synthesis 100 182 .
S.S. Bhagwat, C. Boswell, C. Gude, N. Contardo, D.S. Cohen, J. Mathis, R. Dotson, W. Lee & S. Shetty. (1992) Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 6. 4-substituted 3-pyridinylalkanoic acids.. Bioorganic & Medicinal Chemistry Letters 2:12, pages 1619-1622.
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Ryuji Yoneda, Takahiro Osaki, Shinya Harusawa & Takushi Kurihara. (1990) Dephosphorylation of cyano diethyl phosphates by reduction with lithium–liquid ammonia: an efficient method for conversion of carbonyl compounds into nitriles. J. Chem. Soc., Perkin Trans. 1:3, pages 607-610.
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Ryuji Yoneda, Shinya Harusawa & Takushi Kurihara. (1989) Cyanophosphate: An efficient intermediate for conversion of carbonyl compounds to nitriles. Tetrahedron Letters 30:28, pages 3681-3684.
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M.T. Reetz & H. Müller-Starke. (1984) α-Alkylthio-nitriles via cyanation of thio-acetals and ketals. Tetrahedron Letters 25:31, pages 3301-3304.
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Daan van Leusen & Albert M. van Leusen. (1984) A novel method to build acetyl and hydroxyacetyl side-chains in 17-oxosteroids. Tetrahedron Letters 25:24, pages 2581-2584.
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. 1984. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 353 365 .
Hendrik A. Houwing & Albert M. Van Leusen. (2009) Base‐induced cycloaddition of N ‐(tosylmethyl)imino compounds to michael acceptors. Synthesis of 2,3,4‐trisubstituted pyrroles . Journal of Heterocyclic Chemistry 18:6, pages 1127-1132.
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A. M. VAN LEUSEN & P. G. OOMKES. (2016) ChemInform Abstract: CHEMISTRY OF SULFONYLMETHYL ISOCYANIDES. 20. ONE‐STEP CONVERSION OF ALDEHYDES S TO NITRILES. INTRODUCTION OF A ONE‐CARBON UNIT. Chemischer Informationsdienst 11:37.
Crossref

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