2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides

Iranpoor, Nasser; Baltork, I. M.

doi:10.1016/s0040-4039(00)94616-1

Cited by 83 publications

(16 citation statements)

References 5 publications

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“…[33] Isomeric monoprotected diols, i. e., 2-allyloxy-2-phenylethanol (11) and 2-benzyloxy-2-phenylethanol (13) were prepared by DDQ-catalysed ring opening of 1 with allyl and benzyl alcohol, respectively. [34] 2-Amino-6-(1-azonia-4-azabicyclo[2.2.2]oct-1-yl)purine (2) (DABCO-purine) was obtained by reaction of 2-amino-6-chloropurine (5) with an excess of 1,4-diazabicyclo[2.2.2]octane (DABCO). [18] 4-Vinylphenol (18): 4-Vinylphenyl acetate (2 g, 12.3 mmol) was added to a solution of potassium hydroxide (1.72 g, 32 mmol) in 18 mL of aqueous ethanol (1:1 mixture) and the reaction mixture was stirred for 1.5 h under external cooling with crushed ice.…”

Section: Methodsmentioning

confidence: 99%

Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Novák¹,

Hasník

Linhart

2006

Eur J Org Chem

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A series of O6‐alkyl and ‐arylguanine derivatives that may be formed in vivo after exposure to styrene has been prepared by reaction of 6‐(4‐aza‐1‐azoniabicyclo[2.2.2]octyl)‐purine with alkoxides and aryloxides, respectively. Themonoprotected diols 2‐allyloxy‐ or 2‐benzyloxy‐1‐phenylethanol and 2‐allyloxy‐ or 2‐benzyloxy‐2‐phenylethanol were used as synthetic equivalents of styrene 7,8‐oxide. 4‐Vinylphenol, 2‐(4‐hydroxyphenyl)ethanol and 4‐hydroxyphenylacetic acid were used as synthetic equivalents of arene oxide metabolites of styrene, i. e., styrene 3,4‐oxide, 4‐(2‐hydroxyethyl)benzene 1,2‐oxide and 4‐carboxymethylbenzene 1,2‐oxide, respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Methodsmentioning

confidence: 99%

Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Novák¹,

Hasník

Linhart

2006

Eur J Org Chem

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“…A number of methods using Lewis acids *Corresponding author. E-mail: moghadamm@chem.ui.ac.ir and one-electron transfer catalysts have been also reported for the ring-opening of epoxides with different nucleophiles [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Mohammadpoor‐Baltork

Tangestaninejad

Mirkhani

et al. 2009

JICS

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A highly efficient method for the ring opening of epoxides catalyzed by ZrO(OTf) 2 was adopted. This catalyst efficiently catalyzed alcoholysis, acetolysis and hydrolysis of epoxides and the corresponding alkoxy alcohols, acetoxy alcohols and 1,2-diols were obtained in excellent yields. Conversion of epoxides to 1,2-diacetetes, thiiranes and 1,3-dioxolanes was also performed in the presence of catalytic amounts of ZrO(OTf) 2 , and the corresponding products were obtained in high to excellent yields. The high catalytic activity of ZrO(OTf) 2 is due to the replacement of Cl with OTf, which makes the ZrO(OTf) 2 as efficient Lewis acid.

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“…The ring opening of these compounds in the presence of various nucleophiles leads to the formation of some interesting compounds such as ethers, dioxolanes, and trioxolanes. Various catalysts or photocatalysts such as ceric ammonium nitrate (CAN) [1,2], 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) [3], iron(III) chloride [4], 9,10-dicyanoanthracene (DCA) [5], tetracyanoethylene (TCNE) [6], and 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) [7] have so far been used for this purpose. 7,7,8,8-Tetracyano-p-quinodimethane (TCNQ) has been used as an electron acceptor in many photoinduced electron transfer reactions [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Photoinduced electron transfer ring opening of α-epoxyketones using 7,7,8,8-tetracyano-p-quinodimethane (TCNQ)

Memarian

Nikpour

Sabzyan

2007

JICS

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Photoinduced electron transfer ring opening of -epoxyketones using 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) in methanol and acetic acid solutions resulted in the formation of diastereomeric products, hydroxy ethers and hydroxy esters, respectively. However, the formation of cis-1,3-dioxolanes and cis-spirodioxolanes has been observed on reaction in acetone and cyclohexanone solutions, respectively. The effect of the electron donating character of the substituent influenced the rate of the ring opening. Quantum computational studies explain the mechanism of the addition.

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2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides

Cited by 83 publications

References 5 publications

Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Photoinduced electron transfer ring opening of α-epoxyketones using 7,7,8,8-tetracyano-p-quinodimethane (TCNQ)

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2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides

Cited by 83 publications

References 5 publications

Syntheses of O6‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Syntheses of O6‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

Photoinduced electron transfer ring opening of α-epoxyketones using 7,7,8,8-tetracyano-p-quinodimethane (TCNQ)

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Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides

Syntheses of O⁶‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides