█ _ 0 حصريا كتاب Synthesis of heterocycles by cyclization unsaturated 2024 unsaturated: من كتب علمية Michael J Mealy, William F Bailey Journal Organometallic Chemistry 646 (2002) 59–67 www elsevier com locate jorganchem Account Synthesis unsaturated organolithiums: a review Michael Bailey * Department Chemistry, Uniersity Connecticut, Storrs, CT 06269 3060, USA Received 9 July 2001; accepted 4 September 2001 Abstract The preparation oxygen and nitrogen containing heterocyclic compounds organolithium compounds has been reviewed The review contains 57 references to relevant literature through early 2001 © 2002 Elsevier Science B V All rights reserved Keywords: Intramolecular carbolithiation; Cyclization; Heterocycles; Organolithiums 1 Introduction The from acyclic precursors constitutes one the most studied areas organic chemistry, over past two decades, significant advances have made in exploitation of main group organometallics for this purpose This brief serves highlight major achievements in development anionic olefinic organolithiums as synthetic tool preparation of rings The 5 exo trig hexenyllithiums [1] has received good deal attention route to cyclopentyl systems of carbocycles via organolithiums has [2–4] Surprisingly, development of methodology efficient less It is hoped that survey will provide sufficient insight into nature these species stimulate further growth area chemistry 2 Oxygen heterocycles The first reports carbolithiation an unactivated carbon–carbon double bond a heterocycle appear be brief accounts early 1970s describing intramolecular addition oxyallyllithiums [5] oxybenzyllithiums [5,6] the carbon–carbon norbornene In 1980, Baldwin and co workers observed novel rearrangement of 1 benzofuran 2 upon ortho lithiation and, as illustrated Scheme 1, proposed mechanism the transformation involved of the aryllithium tethered [7] should be noted parent system, (2 propenoxy) phenyllithium (3), rearranges warming the presence TMEDA give 4, however, shown subsequent elimination affords lithium salt cyclopropylphenol [8] systematic studies carbolithiation for heterocycle were the seminal Broka detailing the substituted tetrahydrofurans anionic cyclization olefinic alkoxyorganolithiums [9,10] These cyclizations were found highly stereoselective consequence progression isomerization rigid, chair like transition state analogous hexenyllithium [11,12 مجاناً PDF اونلاين الطريقة العلمية أو المنهج العلمي الثقافة عبارة عن مجموعة التقنيات والطرق المصممة لفحص الظواهر والمعارف المكتشفة المراقبة حديثا من ضمن محتويات القسم : العلماء , أحيائية, بيئية لا خيالية, رياضيات, طب, علم والكثير