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Formation of 3‐Sulfanylcoumarins by SnPh 3 OH‐Promoted Cyclization of 3‐Aryl‐2‐Sulfanylpropenoic Acids
Author(s) -
ÁlvarezBoo Pedro,
Casas José S.,
Couce María D.,
FernándezMoreira Vanesa,
Freijanes Eduardo,
GarcíaMartínez Emilia,
Sordo José,
VázquezLópez Ezequiel
Publication year - 2005
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200500237
Subject(s) - chemistry , sulfanyl , deprotonation , ligand (biochemistry) , denticity , aryl , stereochemistry , medicinal chemistry , crystallography , crystal structure , organic chemistry , ion , biochemistry , receptor , alkyl
Reaction of SnPh 3 OH with 3‐(2‐hydroxyphenyl)sulfanylpropenoic acid [H 2 ( o ‐hpspa)] yielded [SnPh 3 (SC)], where SC is deprotonated 3‐sulfanylcoumarin (3‐sulfanyl‐2H‐1‐benzopyran‐2‐one, HSC), by a cyclization process. Similarly, when 3‐(2‐hydroxy‐5‐bromophenyl)‐ and 3‐(2‐hydroxy‐3,5‐dibromophenyl)‐2‐sulfanylpropenoic acids were treated with the same tin hydroxide, the cyclization resulted in [SnPh 3 (BrSC)] and [SnPh 3 (Br 2 SC)], where BrSC and Br 2 SC are the new ligands formed from the deprotonation of 3‐sulfanyl‐6‐bromocoumarin and 3‐sulfanyl‐6,8‐dibromocoumarin, respectively. The new compounds were characterized by elemental analysis, multinuclear NMR ( 1 H, 13 C and 119 Sn) and vibrational spectroscopy, and mass spectrometry. Single‐crystal X‐ray structures of these complexes all showed that the tin atom is surrounded by three phenyl C atoms and the S and O atoms of the bidentate ligand in a distorted trigonal‐bipyramidal environment. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)