SMALL RING COMPOUNDS IN ORGANIC SYNTHESIS VI by Armin de Meijere (Editor), Armin de Meijere, L. P. Hadjiarapoglou ( 9783662156483 )

Item Details

Title:

SMALL RING COMPOUNDS IN ORGANIC SYNTHESIS VI

By:

Armin de Meijere (Editor), Armin de Meijere, L. P. Hadjiarapoglou

Format:

Paperback

List price:	£109.99
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ISBN 10:

3662156482

ISBN 13:

9783662156483

Publisher:

SPRINGER-VERLAG BERLIN AND HEIDELBERG GMBH & CO. KG

Pub. date:

13 June, 2013

Edition:

Softcover reprint of the original 1st ed. 2000

Series:

Topics in Current Chemistry 207

Pages:

230

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).

Illustrations:

6 Illustrations, black and white; X, 230 p. 6 illus.

Publication:

Germany

Imprint:

Springer-Verlag Berlin and Heidelberg GmbH & Co. K

Returns:

Returnable

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