Bicyclic Cyclopentadienes with N,S Substituents

• Published in: European journal of organic chemistry Vol. 2002; no. 2; pp. 361 - 368
• Main Authors: Wu, He-Ping, Aumann, Rudolf, Fröhlich, Roland, Wegelius, Elina
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2002; WILEY‐VCH Verlag; Wiley
• Subjects: (1-Alkynyl)carbene complexes; 1-Metallahexatrienes; Chemistry; Chemistry, Organic; Chromium; Cyclopentadienes; N,S chelate ligands; Physical Sciences; S chelate ligands; Science & Technology; Tungsten; chromium; 1-METALLA-1,3,5-TRIENES; TRANSITION-METAL-COMPLEXES; ANNULATION; ENAMINES; CR; 1-metallahexatrienes; cyclopentadienes; tungsten; 1-METALLA-1,3-DIENES; (1-alkynyl)carbene complexes; ORGANIC SYNTHESES; N,S chelate ligands
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/1099-0690(20021)2002:2<361::AID-EJOC361>3.0.CO;2-2

Bicyclic cyclopentadienes 5b,c and 12b,c in which an N,S‐chelating group is attached to the cyclopentadiene ring were obtained in good chemical yields by reaction of [1‐alkynyl‐2‐(1‐cycloalkenyl)]carbene complexes 1a−d (M = W, Cr) with pyridine‐2(1H)‐thione (2a) and N‐phenylthioacetamide (2b), respectively. Tetrahydroindene 5b was shown to react with [2‐(1‐cycloalkenyl)ethynyl]carbene complexes 1a−c to give pentacyclic compounds 10a−c by formation of a [4+2] cycloadduct and the subsequent π‐cyclization of its 1‐tungsta‐1,3,5‐hexatriene unit.