Photochromic 1,2-dihetarylethenes with perfluorocyclopentene bridge: Synthesis and spectral and kinetic study

Yarovenko, V. N.; Es'kov, Andrey A.; Semenov, S. L.; Заварзин, И. В.; Kadentsev, V. I.; Kalik, M. A.; Krayushkin, М. М.; Strokach, Yu. P.; Валова, Т. М.; Golotyuk, Z. O.; Barachevsky, V. А.

doi:10.1007/s11172-006-0192-4

Cited by 4 publications

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“…On the other hand, 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an R 3 substituent on the triple bond, R 3 = alkyl, aryl) can also be selectively converted into 2-alkoxymethylbenzothiophenes 5 in fair to excellent yields (49–98%) when allowed to react with an alcohol (also used as the reaction medium) in the presence of AIBN, through a substitutive heterocyclodehydration process taking place under radical conditions. These novel approaches to the synthesis of benzothiophenes 3 and 5 represent convenient alternative methods with respect to the procedures reported so far for their production. , …”

Section: Discussionmentioning

confidence: 99%

Synthesis of Benzothiophene Derivatives by Pd-Catalyzed or Radical-Promoted Heterocyclodehydration of 1-(2-Mercaptophenyl)-2-yn-1-ols

et al. 2011

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Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 1-(2-mercaptophenyl)-2-yn-1-ols 2 or 4, respectively, readily available from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl) ketones 1. In particular, 1-(2-mercaptophenyl)-2-yn-1-ols 2, bearing a CH(2)R substituent on the triple bond (R = alkyl, aryl), were conveniently converted in fair to good yields (55-82%) into (E)-2-(1-alkenyl)benzothiophenes 3 when allowed to react in the presence of catalytic amounts (2 mol %) of PdI(2) in conjunction with KI (KI:PdI(2) molar ratio =10) at 80-100 °C in MeCN as the solvent, through a heterocyclodehydration process. On the other hand, 2-alkoxymethylbenzothiophenes 5 were selectively obtained in fair to excellent yields (49-98%) via a radical-promoted substitutive heterocyclodehydration process, by reacting 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an alkyl or aryl substituent on the triple bond) in alcoholic media at 80-100 °C in the presence of a radical initiator, such as AIBN.

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