cas 17345-61-8, 3,4-Dihydroxybenzonitrile | Articles data

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Mechanism of bromoxynil phototransformation: Effect of medium and surfactant
Bromoxynil (BXN, 3,5-dibromo-4-hydroxybenzonitrile) is a herbicide that is classified as a highly hazardous chemical, toxic for the reproduction. The processes and mechanisms regarding the fate of this compound in the environmental compartments subject to
Bououden, Zelikha,Halladja, Sabrina,Sleiman, Mohamad,Leremboure, Martin,Richard, Claire
p. 151 - 156
(2018)
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Sodium bis(trimethylsilyl)amide in the 'one-flask' transformation of aromatic esters to nitriles
A new 'one-flask' method was developed for the conversion of aromatic esters to the corresponding nitriles by use of sodium bis(trimethylsilyl)amide.
Hwu, Jih Ru,Hsu, Chia Hao,Wong, Fong Fuh,Chung, Chung-Sun,Hakimelahi, Gholam H.
p. 329 - 332
(1998)
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Nitroxygenation of quercetin by HNO
The flavonol quercetin undergoes both enzymatic and non-enzymatic reactions with nitroxyl (HNO/NO-), similar to analogous reactions with dioxygen, but in which N is regioselectively found in the ring-cleaved product. Here we report on kinetic and thermodynamic analysis of the non-enzymatic nitroxygenation reaction in water, which is orders of magnitude faster than the comparable dioxygenation. The second order rate constants were determined from variable temperature reactions, which allowed determination of the reaction activation enthalpy (ΔH≠ = 9.4 kcal/mol), entropy (ΔS≠ = -8.3 cal/mol K), and free energy (ΔG≠ = 11.8 kcal/mol). The determined standard state energy (ΔGo) and activation free energy, as well as the low entropic energy of reaction, are consistent with a proposed single electron transfer (SET) rate determining step.
Han, Xiaozhen,Kumar, Murugaeson R.,Farmer, Patrick J.
p. 399 - 402
(2016)
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Significant enhancement of monooxygenase activity of oxygen carrier protein hemocyanin by urea
Oxygenation of a series of p-substituted phenols to the corresponding catechols (phenolase activity) by the (μ-η2:η2-peroxo)dicopper(II) species of Octopus hemocyanin has been directly examined for the first time by using a UV-vis spectroscopic method in a 0.5 M borate buffer solution containing 8 M urea under anaerobic conditions. Preliminary kinetic studies have indicated that the reaction involves an electrophilic aromatic substitution mechanism as in the case of phenolase reaction of tyrosinase. The oxygenation of phenols by hemocyanin also proceeded catalytically when the reaction was carried out under aerobic conditions. Copyright
Morioka, Chiyuki,Tachi, Yoshimitsu,Suzuki, Shinnichiro,Itoh, Shinobu
p. 6788 - 6789
(2006)
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Method for preparing 3, 4-dihydroxybenzonitrile
The invention discloses a method for preparing 3, 4-dihydroxybenzonitrile, which comprises the following step of: contacting vanillin with hydroxylamine hydrochloride and halide so as to obtain the 3, 4-dihydroxybenzonitrile. The method has the advantages of simplicity in operation, few byproducts, high product yield and the like, thereby being beneficial to industrial production.
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Paragraph 0026; 0032-0043

(2021/07/17)

Selective ether bond breaking method of aryl alkyl ether
The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.
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Paragraph 0194-0196

(2020/09/16)

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal
Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.
Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan
p. 6429 - 6440
(2020/07/14)

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents
Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.
Xiao, Xiao,Greenwood, Nathaniel S.,Wengryniuk, Sarah E.
p. 16181 - 16187
(2019/11/05)

Direct Synthesis of Nitriles from Carboxylic Acids Using Indium-Catalyzed Transnitrilation: Mechanistic and Kinetic Study
Aliphatic and aromatic carboxylic acids can be quantitatively converted to the corresponding nitriles in the presence of catalysts using acetonitrile both as a solvent and reactant at 200 °C. This transformation is based on the acid-nitrile exchange (i.e., transnitrilation) and uses a nontoxic and water resistant catalyst, indium trichloride (InCl3). The mechanism of the transnitrilation was investigated both experimentally and computationally and compared to the previously proposed mechanism. In contrast to the usually assumed formation of amide as an intermediate, transnitrilation is an equilibrium reaction and proceeds via an equilibrated Mumm reaction with the formation of an imide as an intermediate. A simple and reversible mechanism was proposed for this reaction, which was validated by kinetics measurement and by density functional theory calculations of the reaction intermediates and reaction mechanisms.
Vanoye, Laurent,Hammoud, Ahmad,Gérard, Hélène,Barnes, Alexandra,Philippe, Régis,Fongarland, Pascal,De Bellefon, Claude,Favre-Réguillon, Alain
p. 9705 - 9714
(2019/10/14)

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide
Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
Sang, Dayong,Tian, Juan,Tu, Xiaodong,He, Zhoujun,Yao, Ming
p. 704 - 712
(2019/01/23)

Ether bond cracking method of phenylalkyl ether
The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.
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Paragraph 0132-0134

(2018/11/26)

Synthesis method of erlotinib hydrochloride
The invention discloses a synthesis method of erlotinib hydrochloride. The synthesis method comprises the following steps: (1) at a first working section: preparing 3-methoxyl-4-hydroxybenzonitrile from vanillin and hydroxylammonium chloride; (2) at a second working section: synthesizing 3,4-dihydroxybenzonitrile; (3) at a third working section: synthesizing 3,4-di(2-methoxyethoxy)phenylacetonitrile; (4) at a fourth section: synthesizing 4,5-di(2-methoxyethoxy)-2-nitrophenylacetonitrile; (5) at a fifth working section: synthesizing 4,5-di(2-methoxyethoxy)-2-aminophenylacetonitrile hydrochloride; and (6) at a sixth working section: synthesizing the erlotinib hydrochloride. The synthesis method of the erlotinib hydrochloride, disclosed by the invention, has the advantages of reasonable design, easiness of obtaining raw materials, relatively low production cost, simplicity and easiness of operation and is suitable for industrial production.
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(2017/08/31)

Ether bond breakage method for phenylalkyl ethers
The invention discloses an ether bond breakage method for phenylalkyl ethers. The method comprises the step: subjecting the phenylalkyl ethers to an ether bond breakage reaction at the temperature of -20 DEG C to reflux temperature in an organic solvent in the presence of aluminum triiodide and carbodiimide, so as to produce phenols and derivatives thereof. The method is moderate in conditions, simple and convenient in operation, high in yield and wide in applicable phenylalkyl ether range.
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Paragraph 0117-0119

(2017/07/19)

A phenyl alkyl ether ether linkage breaking method (by machine translation)
The invention discloses a phenyl alkyl ether ether linkage breaking method, the method is: in the organic solvent, in the presence of a mineral acid and the aluminium triiodide scavenging agent under the conditions of, phenyl ether in the - 20 °C to reflux temperature lower ether linkage breaking reaction, generating phenol and its derivatives. The mild conditions, the operation is simple, and the yield is high, the applicable phenyl ether range is wide. (by machine translation)
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Paragraph 0071-0073

(2018/04/01)

Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers
A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for the coupling of amines and carboxylic acids to yield amide bonds, are found to be effective hydrogen iodide scavengers that prevent acid-labile groups from deterioration. The method is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho -vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o -hydroxyphenyl ethers.
Sang, Dayong,Wang, Jiahui,Zheng, Yun,He, Jianyuan,Yuan, Caili,An, Qing,Tian, Juan
p. 2721 - 2726
(2017/06/13)

Ether bond rupturing method for ortho-hydroxyl phenyl alkyl ether
The invention discloses an ether bond rupturing method for ortho-hydroxyl phenyl alkyl ether. The method comprises the following steps that in a solvent, an ether bond rupturing reaction occurs to ortho-hydroxyl aryl alky ether at the temperature ranging from minus 20 DEG C to the catalyst reflux temperature under the existence of alkali and a catalyst aluminum triiodide, and catechol and derivatives thereof are generated. The method is simple, reaction conditions are simple, and operation is easy; besides, the yield is high, and the applicable ortho-hydroxyl phenyl alkyl ether range is wide.
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Paragraph 0066; 0067; 0068

(2017/05/27)

Preparation method of 3, 4-dihydroxybenzonitrile
The invention discloses a preparation method of 3, 4-dihydroxybenzonitrile. The method comprises the following steps: taking vanillin as a starting material, enabling vanillin to react with hydroxylamine hydrochloride in a polar solvent at low temperature, and then ensuring that vanillin reacts with hydroxylamine hydrochloride at 50 to 120 DEG C, so as to prepare high-purity Chinese cymbidium nitrile; performing elimination to remove methyl with Lewis acid without separation, so as to obtain high-purity 3, 4-dioxybenzene nitrile in a high yield, with the purity reaching up to 99.0 percent. The method has the advantages that the source of raw materials is wide, the technical process is simple, and pilot scale test shows that 3, 4-dihydroxybenzonitrile is easy for industrial production.
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Paragraph 0038-0041

(2017/09/13)

Pyridine Improves Aluminum Triiodide Induced Selective Cleavage of Alkyl o -Hydroxyphenyl Ethers: A Practical and Efficient Procedure for the Preparation of Hydroxychavicol by Demethylation of Eugenol
Demethylation of eugenol with aluminum triiodide is complicated by an unexpected hydrogenation side reaction. The hydrogenation proceeds through a cascade deprotonation, hydroiodination, and hydrogen-halogen exchange process, and can be prevented by suppressing the hydroiodination in advance. A practical demethylation procedure is thus developed that delivers hydryoxychavicol in essentially quantitative yield by using pyridine as an additive. The method is selective towards cleaving alkyl o-hydroxyphenyl ethers and is compatible with a variety of functional groups.
Sang, Dayong,Yao, Ming,Tian, Juan,Chen, Xiaoman,Li, Li,Zhan, Hongju,You, Linhong
p. 138 - 142
(2016/12/26)

Conversion of Simple Cyclohexanones into Catechols
A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Zou, Miancheng,Tang, Conghui,Liang, Yujie,Song, Song,Jiao, Ning
supporting information
p. 12271 - 12277
(2016/09/28)

Selective ortho-hydroxylation-defluorination of 2-fluorophenolates with a Bis(μ-oxo)dicopper(III) species
The bis(μ-oxo)dicopper(III) species [CuIII 2(μ-O)2(m-XYLMeAN)]2+ (1) promotes the electrophilic ortho-hydroxylation-defluorination of 2-fluorophenolates to give the corresponding catechols, a reaction that is not accomplishable with a (η2:η2-O2) dicopper(II) complex. Isotopic labeling studies show that the incoming oxygen atom originates from the bis(μ-oxo) unit. Ortho-hydroxylation-defluorination occurs selectively in intramolecular competition with other ortho-substituents such as chlorine or bromine. O in, F out: [CuIII2(μ-O) 2(m-XYLMeAN)]2+ is a bis(μ-oxo)dicopper(III) species and promotes the electrophilic ortho-hydroxylation-defluorination of 2-fluorophenolates to give the corresponding catechols. Isotopic labeling shows that the incoming oxygen atom originates from the bis(μ-oxo) unit. Ortho-hydroxylation-defluorination occurs selectively in intramolecular competition with other ortho-substituents such as chlorine or bromine.
Serrano-Plana, Joan,Garcia-Bosch, Isaac,Miyake, Ryosuke,Costas, Miquel,Company, Anna
supporting information
p. 9608 - 9612
(2014/10/15)

Catalytic phenol hydroxylation with dioxygen: Extension of the tyrosinase mechanism beyond the protein matrix
A new catalyst (see structure) hydroxylates phenols with O2 via a stable side-on peroxide complex, which is similar to the active site of tyrosinase in terms of the ligand environment and its spectroscopic properties. The catalytic oxidation of phenols to quinones proceeds at room temperature in the presence of NEt3 and even non-native substrates can be oxidized catalytically. The reaction mechanism is analogous to that of the enzyme-catalyzed reaction. Copyright
Hoffmann, Alexander,Citek, Cooper,Binder, Stephan,Goos, Arne,Ruebhausen, Michael,Troeppner, Oliver,Ivanovic-Burmazovic, Ivana,Wasinger, Erik C.,Stack, T. Daniel P.,Herres-Pawlis, Sonja
supporting information
p. 5398 - 5401
(2013/06/27)

An efficient strategy for protecting dihydroxyl groups of catechols
A novel strategy for protecting dihydroxyl groups of catechols has been developed. Base-mediated cyclizations of catechols with 1,3-dibromopropane provided the corresponding benzo[b]1,4-dioxepans, and herefrom the protecting group was easily cleaved by aluminum chloride. The preparation of the antibacterial and antifungal agent 4-(2-aminothiazol-4-yl)benzene-1,2-diol from catechol reliably verified its availability amenable to various harsh reaction conditions. Georg Thieme Verlag Stuttgart - New York.
Huang, Wei-Bin,Guo, Ying,Jiang, Jian-An,Pan, Xian-Dao,Liao, Dao-Hua,Ji, Ya-Fei
supporting information
p. 741 - 746
(2013/05/09)

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation
A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.
Huang, Chunhui,Ghavtadze, Nugzar,Chattopadhyay, Buddhadeb,Gevorgyan, Vladimir
supporting information; experimental part
p. 17630 - 17633
(2011/12/16)

Ligand-free nickel-catalyzed conversion of aldoximes into nitriles
Catalytic dehydration of aldoximes can be performed efficiently with NiCl2 in acetonitrile under neutral and mild conditions. Under these conditions, various functionalized aldoximes produce the corresponding nitriles in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.
Li, Yen-Ting,Liao, Bei-Sih,Chen, Hsin-Pei,Liu, Shiuh-Tzung
experimental part
p. 2639 - 2643
(2011/10/04)

Sodium bis(trimethylsilyl)amide in the oxidative conversion of aldehydes to nitriles
The feasibility of the Me3Si species acting as a nucleofuge was investigated in compounds containing the NSiMe3 moiety. Treatment of various aromatic aldehydes with 2.2 equiv. of NaN(SiMe3)2 at 185°C in a sealed tube produced the corresponding nitriles in high yields (81-98%). In these reactions, NaN(SiMe3)2 acted as an oxidizing agent. Results from control experiments indicate that the Me 3Si unit can depart efficiently from the NSiMe3 moiety of N-silylimine intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Jih, Ru Hwu,Fung, Fuh Wong
p. 2513 - 2516
(2007/10/03)

Process for preparing 3,4-dihydroxy-benzonitrile
A process for preparing 3,4-dihydroxybenzonitrile includes the steps of reacting a nitrile compound with an alkali metal halide, followed by treating with an acid.
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Page 2-3

(2008/06/13)

A Selective and Mild Oxidation of Primary Amines to Nitriles with Trichloroisocyanuric Acid
An efficient and highly selective method for the oxidative conversion of primary amines to the corresponding nitriles using trichloroisocyanuric acid in the presence of catalytic TEMPO under mild reaction conditions is described. Other functional groups such as C,C-double bonds, benzyloxy etc. were found to be unaffected under the reaction conditions. This procedure provides a new entry to the synthesis of various aliphatic, aromatic and heterocyclic nitriles in excellent yield.
Chen, Fen-Er,Kuang, Yun-Yan,Dai, Hui-Fang,Lu, Liang,Huo, Ming
p. 2629 - 2631
(2007/10/03)

Tetrabutylammonium peroxydisulfate in organic synthesis; XIII.1 A simple and highly efficient one-pot synthesis of nitriles by nickel-catalyzed oxidation of primary alcohols with tetrabutylammonium peroxydisulfate
A facile one-pot method is presented for the synthesis of nitriles from the corresponding primary alcohols by nickel-catalyzed oxidation with tetrabutylammonium peroxydisulfate in the presence of ammonium hydrogen carbonate under basic aqueous conditions. This convenient synthetic method provides an easy and simple access to various aliphatic, aromatic and heterocyclic nitriles in excellent yields with very high purity.
Chen, Fen-Er,Li, Yong-Ye,Xu, Mei,Jia, Hui-Qing
p. 1804 - 1806
(2007/10/03)

A simple and highly efficient one-pot chemoselective synthesis of nitriles from aldehydes: Mechanistic insight and selectivity control through modulation of electronic and steric factors
Aldehydes are converted into nitriles in a one-pot reaction by treatment with H2NOH·HCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavage (e.g. methoxy, benzyloxy) or aromatic nucleophilic substitution (e.g. nitro or chloro) takes place for substrates beating such functionalities. Electronic and steric factors around the aldehyde carbon affect the rate of nitrile formation. Excellent to moderate selectivity is observed during intermolecular competition between pair of aldehydes with varying electronic and steric requirements.
Chakraborti,Kaur,Roy
p. 1000 - 1006
(2007/10/03)

One-pot synthesis of nitriles from aldehydes under microwave irradiation: Influence of the medium and mode of microwave irradiation on product formation
Chemoselective transformation of aldehyde to nitrile takes place in a one-pot reaction by treatment with H2NOHHCl in N- methyl-2-pyrrolidinone (NMP) under microwave irradiation using convection mode.
Chakraborti, Asit K.,Kaur, Gurmeet
p. 13265 - 13268
(2007/10/03)

Nitration and hydroxylation of substituted phenols by peroxynitrite. Kinetic feature and an alternative mechanistic view
The reaction of peroxynitrite (ONOO-) with a series of para-substituted phenols has been examined in aqueous phosphate buffer and acetonitrile solutions. Major products were the corresponding 2-nitro derivative and the 4-substituted catechol. Kinetic study showed good correlation with Hammett σ(p)+ parameters and reduction potentials, suggesting the possible one-electron transfer process involving the nitrosoniun ion (NO+) as initial electrophile generated from peroxynitrous acid.
Nonoyama, Nobuaki,Chiba, Kazuhiko,Hisatome, Kaori,Suzuki, Hitomi,Shintani, Futoshi
p. 6933 - 6937
(2007/10/03)

One-step conversion of aldehydes into nitriles in dry media under microwave irradiation
Aldehydes undergo rapid reaction with hydroxylammonium chloride using HCOOH/SiO2 as solid support catalyst, under microwave irradiation without solvent to affords nitriles in 60-90% yields.
Feng, Jun-Cai,Liu, Bin,Dai, Li,Bian, Ning-Sheng
p. 3765 - 3768
(2007/10/03)

Sodium Bis(trimethylsily)amide and Lithium Diisopropylamide in Deprotection of Alkyl Aryl Ethers: α-Effect of Silicon
Removal of methyl, benzyl, and methylene groups from alkyl aryl ethers is among the most popular deprotecting methods in organic synthesis. Alkali organoamides NaN(SiMe3)2 and LiN(i-Pr)2, often used as organic bases, have been developed as efficient deprotecting agents. Treatment of aryl methyl ethers with 1.5 equiv of NaN(SiMe3)2 or LiN(i-Pr)2 in THF and 1,3-dimethyl-2-imidazolidinone in a sealed tube at 185 °C produced the corresponding phenol derivatives in good to excellent yields (80-97percent). Removal of the methylene unit from benzodioxole derivatives was also accomplished by use of 2.5 equiv of these alkali organoamides. The corresponding catechols were obtained in 93-99percent yields. The activity of NaN(SiMe3)2 was proven lower than that of LiN(i-Pr)2; it is due to the steric congestion and the α-stabilizing effect of the silyl groups. Thus selective mono-O-demethylation of o-dimethoxybenzenes can be achieved by the use of NaN(SiMe3)2 but not LiN(i-Pr)2. O-Debenzylation of aryl benzyl ethers, however, can be accomplished by the use of LiN(i-Pr)2.
Hwu, Jih Ru,Wong, Fung Fuh,Huang, Jiann-Jyh,Tsay, Shwu-Chen
p. 4097 - 4104
(2007/10/03)

Regioselective ring opening by propanethiolate of (methylenedioxy)benzenes with electron-withdrawing substituents
The ring opening reaction of (methylenedioxy)benzenes 1 with propanethiolate in DMF leads to products 2 and/or 3, depending on the nature of the electron-withdrawing substituent Z.
Cassels, Bruce K.,Radetski, Claudemir,Rezende, Marcos Caroli
p. 448 - 450
(2007/10/02)