Small Ring Compounds in Organic Synthesis VI Paperback / softback
Edited by Armin de Meijere
Part of the Topics in Current Chemistry series
Paperback / softback
Description
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).
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Item not Available
- Format:Paperback / softback
- Pages:230 pages, 6 Illustrations, black and white; X, 230 p. 6 illus.
- Publisher:Springer-Verlag Berlin and Heidelberg GmbH & Co. K
- Publication Date:13/06/2013
- Category:
- ISBN:9783662156483
Information
-
Item not Available
- Format:Paperback / softback
- Pages:230 pages, 6 Illustrations, black and white; X, 230 p. 6 illus.
- Publisher:Springer-Verlag Berlin and Heidelberg GmbH & Co. K
- Publication Date:13/06/2013
- Category:
- ISBN:9783662156483
