Small Ring Compounds in Organic Synthesis VI - Couverture souple

Couverture souple

ISBN 10 : 3662156482 ISBN 13 : 9783662156483

Editeur : Springer, 2013

Synopsis

Since the pioneering work by Sarel and co-workers on the iron carbonyl p- moted transformation of vinylcyclopropanes and related compounds [1], a - riety of transition metal complexes have been examined to achieve effective - tivation of the vinylcyclopropane-cyclopentene rearrangement which usually requires pyrolytic conditions. These reactions have been applied to natural product synthesis in some cases and have already been reviewed in several - cellent articles [2-4]. Contrary to the well-established chemistry of the vinylcyclopropanes, the corresponding reactions of alkynyl- and propadienylcyclopropanes have not, until recently, received much attention.We present here a summary of the recent efforts towards the development of transition metal promoted transformation of these molecules with a brief survey of the corresponding thermal reactions. 2 Rearrangement of Alkynylcyclopropanols Unlike the well-known chemistry of the vinylcyclopropane-cyclopentene - arrangement, there is no general method for the rearrangement of alkyn- cyclopropane to cyclopentene derivatives.One specific example is the pyrolysis of 1-ethynyl-2-methylcyclopropane to methylenecyclopentene and other c- pounds [5].At 530°C, 1-ethynyl-2-methylcyclopropane (1) undergoes a [1, - hydrogen shift to give hexa-1,2,5-triene ( 2), which further isomerizes to met- lenecyclopentenes 3 and 4 in 38 and 29% yield, respectively (Scheme 1).

Détails de l'édition

• Éditeur: Springer
• Date d'édition: 2013
• Langue: anglais
• ISBN 10: 3662156482
• ISBN 13: 9783662156483
• Reliure: Broché
• Nombre de pages: 244
• Éditeur: Meijere Armin De
• Coordonnées du fabricant: ProductSafety@springernature.com; ProductSafety@springernature.com; ; Poststr. 9; Darmstadt; 64293; Allemagne