ChemInform Abstract: Radical Telomerization of Ethylene with 2‐Methyl‐1,3‐benzodioxolane.

Bikbulatov, R. R.; Timofeeva, T. V.; Zorina, L. N.; Safiev, O. G.; Zorin, V. V.; Rakhmankulov, D. L.

doi:10.1002/chin.199619130

Cited by 2 publications

(4 citation statements)

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“…10 %) when in the presence of TBADT (2 mol %), although no byproducts were detected by GC analysis. Moreover, in the absence of TBADT, 1 was likewise unreactive when irradiated in the presence of acrylonitrile (9).…”

Section: Resultsmentioning

confidence: 95%

“…Spectroscopic data of compound 5 are in accordance with the literature. [37] Compounds 2, [38] 7, [39] 8, [9] 13, [40] 14, [41] and 17 [42] were synthesized according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

“…These compounds are usually prepared by condensation of a (substituted) catechol and a carbonyl derivative, [7,8] although the method is unsatisfactory when using low-boiling aldehydes or ketones. [9] The alternative derivatization at position 2 of the preformed 1,3-benzodioxole ring has likewise been applied with some success for the introduction of a chlorine or of a O-bonded substituent. [10,11] The introduction of a C-bonded substituent has been rarely reported (see the Discussion Section).…”

Section: Introductionmentioning

confidence: 99%

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Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Ravelli

Albini

Fagnoni

2010

Chemistry A European J

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A mild and general method for the synthesis of potentially bioactive 2-substituted-1,3-benzodioxoles is presented. This is based on the photocatalyzed activation of methylene hydrogen atoms in the presence of tetrabutylammonium decatungstate (TBADT). The method gave yields ranging from 46-77 % with no interference by benzene ring substituents, such as OR, COOMe, Me, or CHO. The OH group interfered, but protection regenerated the reactivity. 5-Chloro-1,3-benzodioxole was converted into a safrole derivative through a one-pot process involving two consecutive irradiations, at 366 nm for the photocatalyzed alkylation at position 2 and at 310 nm for the alkylation at position 5.

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Section: Resultsmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Ravelli

Albini

Fagnoni

2010

Chemistry A European J

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“…Tetrachlorocatechol and 3,5-di-tert-butylcatechol were purchased from Sigma-Aldrich and used as received. The ligand N,N′-(mesityl)phenanthrene-9,10-diimine (pdi) 32 and the starting material (MeCN) 2 PdCl 2 33 were prepared by previously described methods as were 2,2-dimethyl-1,3-benzodioxole 34 (2) and ethyl 3,4dihydroxybenzoate (5). 35 Physical Methods.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups

et al. 2015

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New catecholate ligands containing protected phosphonate anchoring groups in the 4-position of the catecholate ring were synthesized. The catechol 4-diethoxyphosphorylbenzene-1,2-diol, ((Et)phoscat)H2, was prepared in three steps from pyrocatechol; whereas, the catechol 4-(diethoxyphosphorylmethyl)benzene-1,2-diol, ((Et)Bnphoscat)H2, containing a methylene spacer between the catecholate ring and phosphonate anchor, was prepared from protocatechuic acid in six linear steps. Both catechol derivatives were further elaborated to their trimethylsilyl-protected counterparts to facilitate their binding to nanocrystalline metal oxides. Electronic spectroscopy and cyclic voltammetry were used to probe the electronic properties of the phosphonate-functionalized catecholates in charge-transfer complexes of the general formula (catecholate)Pd(pdi) (pdi = N,N'-bis(mesityl)phenanthrene-9,10-diimine). These studies show that attachment of the phosphonate anchor directly to the 4-position of the ((Et)phoscat)(2-) ligand significantly perturbs the donor ability of the catecholate ligand; however, incorporation of a single methylene spacer group in ((Et)Bnphoscat)(2-) helps to isolate catecholate from the electron-withdrawing phosphonate group.

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ChemInform Abstract: Radical Telomerization of Ethylene with 2‐Methyl‐1,3‐benzodioxolane.

Cited by 2 publications

References 0 publications

Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups

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