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Organic Synthess - McKusick B.C.

McKusick B.C., Boekelheide V., Emmons W.D. Organic Synthess - New York, 1963. - 134 p.
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Procedures should be written in the style and format employed Ш the latest published volume of Organic Syntheses. Copies of
vi NOMENCLATURE
the current style sheet may be obtained from the Secretary of the Editorial Board. In Section 3, Methods of Preparation, there should be described other practical methods for preparing the compound which have appeared in the literature. It is unnecessary to mention methods which have been published but are of no practical synthetic value. In Section 4, Merits of the Preparation, a statement should be made indicating why the preparation is published in Organic Syntheses. Among the obvious reasons for publication would be the novelty of the procedure, general scope of the synthetic method, specific interest in the compound or its use as an intermediate for preparing other compounds, convenience of the method, and improvement in yields. Two copies of each procedure should be submitted to the Secretary of the Editorial Board. It is sometimes helpful to the Board if there is an accompanying letter setting forth the features of the preparation which are of interest.
Additions, corrections, and improvements to the preparations previously published are welcomed and should be directed to the Secretary.
EDITOR’S PREFACE
Organic Syntheses was founded by Roger Adams, Hans T. Clarke, James B. Conant, and Oliver Kamm in 1921. At that time few compounds could be bought and, in the words of the preface in Volume 1, “the preparation of materials for research, always time consuming and annoying,” was “made increasingly so by the inexactness of the published information, which so often omits essential details.” Organic Syntheses was founded primarily to provide research chemists with detailed, reproducible “methods of preparation of some of the most needed organic chemical reagents,” and it is a measure of the progress chemical technology has made since 1921 that, when Volume 1 was published, allyl alcohol, furfural, and trimethylamine were among the compounds for which good directions were urgently needed by research chemists. The procedures of Organic Syntheses also served as models for carrying out various types of reactions, but that was a secondary aim in the early years.
Although there are some 1400 procedures in the 43 volumes that have appeared annually since the founding, there is no sign that the supply of suitable procedures is running out. However, there has been a gradual change in emphasis in the types published. This change has come about because the number of commercially available compounds has risen steadily during the 43 years of Organic Syntheses’ history and is now in the thousands. As a result, the need7 for procedures describing specific compounds has decreased relative to the need for those illustrating general reactions. This trend is particularly evident in recent volumes of Organic Syntheses, which have emphasized examples of relatively new reactions of general usefulness.
In the present volume, easily three-fourths of the preparations fall into this class. Thus the preparation of docosanedioic acid (p- 34) demonstrates how acylation of an enamine can be used to prepare long-chain acids. The preparation of N-nitromorpholine
viii
EDITOR’S PREFACE
(p. 83) shows a general way of putting a nitro group on the nitrogen of secondary amines. Three general types of cyclo-addition are illustrated: addition of an allene to an alkene (dimethyl 3-methylenecyclobutane-l,2-dicarboxylate, p. 27), addition of a fluoroolefin to an alkene (l-chIoro-l,4,4-tri-fluorobutadiene, p. 17), and addition of a chlorophosphine to a 1,3-diene (3-methyl-l-phenyl-l-phospha-3-cyclopentene 1-oxide, p. 73). Improved versions of the Schiemann reaction (1-bromo-
2-fluorobenzene, p. 12) and the Hunsdiecker reaction (bromo-cyclopropane, p. 9) exemplify modem methods of introducing halogen into molecules. 1,4-Dihydrobenzoic acid (p. 22) illustrates the Birch reduction.
The chief value of several procedures lies in current research interest in the products. Tropylium fluoborate (p. 101) is a good example.
I appreciate the help in assembling this volume that I received from Dr. Norman G. Fisher, who advised me on nomenclature, Dr. Wallace Copeland, who checked most of the references, and Mrs. Irene Dutton, who typed the manuscript and checked proof.
Blaine C. McKtjsick
CONTENTS
1-Aminopyridinium Iodide..........................................1
a-BENZYLrDENE-7-PHENVL-A^’1'-BUTEN0LIDE............................3
2-BROMOALLYL AMINE................................................6
Bromocyclopropane................................................9
I-Bromo-2-fluorobenzene..........................................12
9-Chloroanthracene................................................IS
1-Ckloro-1,4,4-texfluorobctaoien e..................................17
1,4-Dihydrobenzoic Acid............................................22
«-N,N-DlMETHYLAM:iNOPHENYLACETONITRILE............................25
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