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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 16
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Original Articles

Efficient Dehydration of Aldoximes to Nitriles with TiCl3(OTf)

N. Iranpoor Chemistry Department, Shiraz University, Shiraz, 71454, Iran
&
B. Zeynizadeh Chemistry Department, Shiraz University, Shiraz, 71454, Iran
Pages 2747-2752 | Received 24 Sep 1998, Published online: 25 Sep 2007

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Pranab Ghosh, Gyan Chandra Pariyar, Bittu Saha & Raju Subba. (2016) FeCl3-silica: A green approach for the synthesis of nitriles from oximes. Synthetic Communications 46:8, pages 685-691.
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KalpeshD. Parghi, JitendraR. Satam & RadhaV. Jayaram. (2011) Silica supported heteropolyacid catalyzed dehydration of aldoximes to nitriles and alcohols to alkenes. Green Chemistry Letters and Reviews 4:2, pages 143-149.
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Mohammad Navid Soltani Rad, Ali Khalafi-Nezhad, Somayeh Behrouz, Zohreh Amini & Marzieh Behrouz. (2010) Simple and Highly Efficient Procedure for Conversion of Aldoximes to Nitriles Using N-(p-Toluenesulfonyl) Imidazole. Synthetic Communications 40:16, pages 2429-2440.
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Kieseung Lee, Sang‐Bae Han, Eun‐Mi Yoo, Soon‐Ryang Chung, Haibum Oh & Sungwan Hong. (2004) Efficient Transformation of Aldoximes to Nitriles Using 2‐Chloro‐1‐methylpyridinium Iodide Under Mild Conditions. Synthetic Communications 34:10, pages 1775-1782.
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N. Iranpoor, H. Firouzabadi & G. Aghapour. (2002) A RAPID AND FACILE CONVERSION OF PRIMARY AMIDES AND ALDOXIMES TO NITRILES AND KETOXIMES TO AMIDES WITH TRIPHENYLPHOSPHINE AND N-CHLOROSUCCINIMIDE. Synthetic Communications 32:16, pages 2535-2541.
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Articles from other publishers (25)

Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 85 .
Xiaobi Jing, Tingting Wang, Yuanhua Ding & Lei Yu. (2017) A scalable production of anisonitrile through organoselenium-catalyzed dehydration of anisaldoxime under solventless conditions. Applied Catalysis A: General 541, pages 107-111.
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Songzhu Xing, Qiuxia Han, Zhuolin Shi, Shugai Wang, PeiPei Yang, Qiang Wu & Mingxue Li. (2017) A hydrophilic inorganic framework based on a sandwich polyoxometalate: unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine. Dalton Transactions 46:35, pages 11537-11541.
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Kengo Hyodo, Saki Kitagawa, Masayuki Yamazaki & Kingo Uchida. (2016) Iron‐Catalyzed Dehydration of Aldoximes to Nitriles Requiring Neither Other Reagents Nor Nitrile Media. Chemistry – An Asian Journal 11:9, pages 1348-1352.
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Javad Azizian, Parviz Torabi & Jalil Noei. (2016) Synthesis of benzimidazoles and benzoxazoles using TiCl3OTf in ethanol at room temperature. Tetrahedron Letters 57:2, pages 185-188.
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Monireh Zarghani & Batool Akhlaghinia. (2015) Copper immobilized on aminated ferrite nanoparticles by 2-aminoethyl dihydrogen phosphate (Fe 3 O 4 @AEPH 2 -Cu II ) catalyses the conversion of aldoximes to nitriles . Applied Organometallic Chemistry 29:10, pages 683-689.
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Bo Wu, Xiang Gao, Mu-Wang Chen & Yong-Gui Zhou. (2014) A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o -Quinone Methides Generated from 2-(1-Tosylalkyl)phenols . Chinese Journal of Chemistry 32:10, pages 981-984.
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Ali Khalafi-Nezhad & Somayeh Mohammadi. (2014) Chitosan supported ionic liquid: a recyclable wet and dry catalyst for the direct conversion of aldehydes into nitriles and amides under mild conditions. RSC Advances 4:27, pages 13782.
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Dharm Dev, Nani Babu Palakurthy, Nitesh Kumar & Bhubaneswar Mandal. (2013) An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: a mechanistic perception. Tetrahedron Letters 54:33, pages 4397-4400.
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Shintaro Itagaki, Keigo Kamata, Kazuya Yamaguchi & Noritaka Mizuno. (2013) A Monovacant Lacunary Silicotungstate as an Efficient Heterogeneous Catalyst for Dehydration of Primary Amides to Nitriles. ChemCatChem 5:7, pages 1725-1728.
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Madabhushi Sridhar, Mallu Kishore Kumar Reddy, Vangipuram Venkata Sairam, Jillella Raveendra, Kondal Reddy Godala, Chinthala Narsaiah, Beeram China Ramanaiah & Cirandur Suresh Reddy. (2012) Acetohydroxamic acid: a new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst. Tetrahedron Letters 53:27, pages 3421-3424.
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Jalil Noei, Ahmad Reza Khosropour & Arsalan Mirjafari. (2012) The Combination of 1-Butyl-3-methylimidazolium Bromide and Trichloro(trifluoromethanesulfonato)titanium(IV) as a New Protocol for the Synthesis of Aryl Nitriles. Bulletin of the Korean Chemical Society 33:6, pages 2102-2104.
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Lal Dhar S. Yadav, Vishnu P. Srivastava & Rajesh Patel. (2009) Bromodimethylsulfonium bromide (BDMS): a useful reagent for conversion of aldoximes and primary amides to nitriles. Tetrahedron Letters 50:39, pages 5532-5535.
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Nagnnath D. Kokare & Devanand B. Shinde. (2008) Efficient conversion of aldoximes to nitriles using phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester. Monatshefte für Chemie - Chemical Monthly 140:2, pages 185-188.
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Pitchiah Tamilselvan, Yeriyur B. Basavaraju, Ellappan Sampathkumar & Ramachandran Murugesan. (2009) Cobalt(II) catalyzed dehydration of aldoximes: A highly efficient practical procedure for the synthesis of nitriles. Catalysis Communications 10:5, pages 716-719.
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Jalil Noei & Ahmad R. Khosropour. (2008) TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes. Tetrahedron Letters 49:49, pages 6969-6971.
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Kazuya Yamaguchi, Hiroshi Fujiwara, Yoshiyuki Ogasawara, Miyuki Kotani & Noritaka Mizuno. (2007) A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles. Angewandte Chemie International Edition 46:21, pages 3922-3925.
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Kazuya Yamaguchi, Hiroshi Fujiwara, Yoshiyuki Ogasawara, Miyuki Kotani & Noritaka Mizuno. (2007) A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles. Angewandte Chemie 119:21, pages 3996-3999.
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Yoshiro Furuya, Kazuaki Ishihara & Hisashi Yamamoto. (2007) Perrhenic Acid-Catalyzed Dehydration from Primary Amides, Aldoximes, N -Monoacylureas, and α-Substituted Ketoximes to Nitrile Compounds . Bulletin of the Chemical Society of Japan 80:2, pages 400-406.
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Zhijay Tu, Yaochung Jang, Chunchi Lin, Ju-Tsung Liu, Jianming Hsu, M.N.V. Sastry & Ching-Fa Yao. (2005) The study of reaction mechanism for the transformation of nitronate into nitrile by phosphorus trichloride. Tetrahedron 61:44, pages 10541-10551.
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Majid M. Heravi, Khadijeh Bakhtiari, Rahim Hekmat Shoar & Hossein A. Oskooie. (2019) DABCO–POCl 3 , a Mild Dehydrating Agent for the Preparation of Nitriles from Aldoximes . Journal of Chemical Research 2005:9, pages 590-591.
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Anastassiya V Makarycheva-Mikhailova, Nadezhda A Bokach, Matti Haukka & Vadim Yu Kukushkin. (2003) The first example of ligand-mediated dehydration of aldoximes. Inorganica Chimica Acta 356, pages 382-386.
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Michael B. Smith. 2003. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 417 424 .
Soon Ha Yang & Sukbok Chang. (2001) Highly Efficient and Catalytic Conversion of Aldoximes to Nitriles. Organic Letters 3:26, pages 4209-4211.
Crossref
N. Iranpoor & B. Zeynizadeh. (2010) ChemInform Abstract: Efficient Dehydration of Aldoximes to Nitriles with TiCl 3 (OTf). . ChemInform 30:40.
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