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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 7
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Original Articles

A MILD AND EFFICIENT CLEAVAGE OF gem-DIACETATES TO ALDEHYDES BY CBr4*

T. Ramalingam Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
R. Srinivas Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
B. V. Subba Reddy Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
J. S. Yadav Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
Pages 1091-1095 | Received 07 Apr 2000, Published online: 09 Nov 2006

Citations (23)

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Gaurav Bartwal, Mohit Saroha & Jitender M. Khurana. (2018) Nickel boride mediated chemoselective deprotection of 1,1-diacetates to aldehydes and deprotection with concomitant reduction to alcohols at ambient temperature. Synthetic Communications 48:1, pages 97-103.
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Bandita Datta & M.A. Pasha. (2011) Chemoselective Protection and Deprotection of Aldehydes Using Solid Supported Reagent (Silica Chloride) Under Solvent-Free Conditions. Synthetic Communications 41:8, pages 1160-1166.
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Fuyi Zhang, Hong Liu, Qing-Ju Zhang, Yu-Fen Zhao & Feng-Ling Yang. (2010) Silica Phosphoric Acid: An Efficient and Recyclable Catalyst for the Solvent-Free Synthesis of Acylals and Their Deprotection in MeOH. Synthetic Communications 40:21, pages 3240-3250.
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Majid M. Heravi, Fatemeh Derikvand & Fatemeh F. Bamoharram. (2006) Dodecatungstophosphoric Acid (H3PW12O40): A Novel and Efficient Recyclable Catalyst for Synthesis of 1,1‐Diacetates from Aromatic Aldehydes in Solvent‐Free System and Their Deprotection. Synthetic Communications 36:21, pages 3109-3115.
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G. P. Romanelli, J. C. Autino, G. Baronetti & H. J. Thomas. (2004) A Fast and Efficient Deprotection of Aldehydes from Acylals Using a Wells‐Dawson Heteropolyacid Catalyst (H6P2W18O62 · 24H2O). Synthetic Communications 34:21, pages 3909-3914.
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Articles from other publishers (18)

Dominik Koszelewski & Ryszard Ostaszewski. (2019) The studies on chemoselective promiscuous activity of hydrolases on acylals transformations. Bioorganic Chemistry 93, pages 102825.
Crossref
. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 554 685 .
Farhad Shirini, Zahra Neyestani & Masoumeh Abedini. (2009) KBrO3/MoO3: An efficient reagent system for the oxidative deprotection of semicarbazones, 1,1-diacetates and acetals. Chinese Chemical Letters 20:5, pages 514-518.
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Antonio Procopio, Marco Gaspari, Monica Nardi, Manuela Oliverio & Roberto Romeo. (2008) MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates. Tetrahedron Letters 49:12, pages 1961-1964.
Crossref
Lucjan Strekowski, Alexander S. Kiselyov, Andrey A. Fokin & Peter R. Schreiner. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Ming-Chung Yan, Yeng-Nan Chen, Huan-Ting Wu, Chang-Ching Lin, Chien-Tien Chen & Chun-Cheng Lin. (2006) Removal of Acid-Labile Protecting Groups on Carbohydrates Using Water-Tolerant and Recoverable Vanadyl Triflate Catalyst. The Journal of Organic Chemistry 72:1, pages 299-302.
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Uday V. Desai, T.S. Thopate, D.M. Pore & P.P. Wadgaonkar. (2006) An efficient, solvent-free method for the chemoselective synthesis of acylals from aldehydes and their deprotection catalyzed by silica sulfuric acid as a reusable solid acid catalyst. Catalysis Communications 7:7, pages 508-511.
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Hossein Eshghi & Parvaneh Shafieyoon. (2005) P 2 O 5 /SiO 2 as an Efficient Reagent for Selective Deprotection of 1,1-Diacetates under Solvent-Free Conditions . Journal of the Chinese Chemical Society 52:1, pages 155-157.
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Zhan-Hui Zhang, Liang Yin, Yi Li & Yong-Mei Wang. (2005) A practical and efficient procedure for the cleavage of acylals to aldehydes catalyzed by indium tribromide in water. Tetrahedron Letters 46:5, pages 889-893.
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Veerababurao Kavala & Bhisma�K. Patel. (2005) Reinvestigation of the Mechanism ofgem-Diacylation: Chemoselective Conversion of Aldehydes to Variousgem-Diacylates and Their Cleavage under Acidic and Basic Conditions. European Journal of Organic Chemistry 2005:2, pages 441-451.
Crossref
Ming-Yi Chen, Laxmikant N. Patkar, Kuo-Cheng Lu, Adam Shih-Yuan Lee & Chun-Cheng Lin. (2004) Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions. Tetrahedron 60:50, pages 11465-11475.
Crossref
Hongying Niu, Xinying Zhang, Haiming Guo & Jianji Wang. (2019) A mild and efficient deprotection of geminal diacetates catalysed by FeCl 3 ·6H 2 O in ionic liquid . Journal of Chemical Research 2004:11, pages 764-765.
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Zhan-Hui Zhang. (2019) Indium tribromide/[bmim]PF 6 : A novel and recyclable catalytic system for the deprotection of 1,1-diacetates . Journal of Chemical Research 2004:11, pages 753-755.
Crossref
Ming-Yi Chen, Laxmikant N. Patkar, Mi-Dan Jan, Adam Shih-Yuan Lee & Chun-Cheng Lin. (2004) CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups. Tetrahedron Letters 45:3, pages 635-639.
Crossref
G Smitha & Ch.Sanjeeva Reddy. (2003) A facile and efficient ZrCl 4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage. Tetrahedron 59:48, pages 9571-9576.
Crossref
Michael B. Smith. 2003. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 90 114 .
Alan C. Spivey & David Leese. (2002) 2  Synthetic methods : Part (iii) Protecting groups. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 98, pages 41-60.
Crossref
T. Ramalingam, R. Srinivas, B. V. Subba Reddy & J. S. Yadav. (2010) ChemInform Abstract: A Mild and Efficient Cleavage of gem‐Diacetates to Aldehydes by CBr 4 . . ChemInform 32:42.
Crossref

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