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Facile Ring‐Expansion Substitution Reactions of 1,3‐Dithiolanes and 1,3‐Dithianes Initiated by Electrophilic Reagents to Produce Monohalo‐, ‐cyano‐, ‐azido‐ and ‐thiocyanato‐1,4‐dithiins and ‐1,4‐dithiepins
Author(s) -
Firouzabadi Habib,
Iranpoor Nasser,
Garzan Atefeh,
Shaterian Hamid Reza,
Ebrahimzadeh Farzaneh
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400502
Subject(s) - chemistry , electrophile , reagent , electrophilic substitution , ring (chemistry) , aryl , substitution reaction , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
Mild and convenient methods for the high yielding ring‐expansion substitution reactions of 1,3‐dithiolanes and 1,3‐dithianes generated from different aryl methyl ketones using different electrophilic reagents are reported. In this study, facile preparations of monohalo‐, ‐cyano‐, ‐azido‐, ‐thiocyanato‐1,4‐dithiins and ‐1,4‐dithiepins are described. A general mechanism is also proposed for the reactions described in this article. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)