Organic Syntheses Procedures

Geranyl chloride was prepared by treating geraniol, available from Aldrich Chemical Company, with carbon tetrachloride and triphenyl phosphine according to an Organic Syntheses procedure (Calzada, J. G. Hooz, J. Org. Si nth, 1974, 54, 63). 

M. Freifelder, Calalytic Hydrogenation in Organic Syntheses. Procedures and Commen-lary," p. 5. Wiley, New York, 1978. 

Chemists are invited to submit for publication in Organic Syntheses procedures for the preparation of compounds which are of general interest or which illustrate useful synthetic methods. The procedures submitted should represent, as nearly as possible, optimum conditions for the preparations, and should have been checked carefully by the submitter. Full details of all steps in the procedure should be included, and the range of yields should be reported rather than the maximum yield obtainable. The melting point of each solid product should be given, and the boiling-point range and refractive index (at 25°) of each liquid product. The method of preparation or source of the reactants and the criteria for the purity of the products should be stated. 

Trifluoromethanesulfonlc anhydride was purchased from the Aldrich Chemical Company, Inc., and used as received. It can also be prepared from the acid according to the Organic Syntheses procedure.4... 

Dimethyl benzalmalonate and the corresponding esters of other alcohols can be prepared according to an Organic Syntheses procedure or as described In standard textbooks.2... 

Organic Syntheses welcomes and encourages submission of experimental procedures which lead to compounds of wide interest or which Illustrate Important new developments in methodology. The Editorial Board will consider proposals in outline formal as shown below, and will request full experimental details for those proposals which are of sufficient interest. Tear-out copies of this form may be found at the back of this volume. Submissions which are longer than three steps from commercial sources or from existing Organic Syntheses procedures will be accepted only in unusual circumstances. 

The aldehyde was freshly distilled material prepared according to the Organic Syntheses procedure.2... 

The removal of excess thionyl chloride by formation of an azeotrope with benzene was used in a previous Organic Syntheses procedure 6 however, toluene is much less toxic than benzene and is therefore recommended. 

The following Organic Syntheses procedure illustrates one of the uses of the 4-carbon organosilane intermediates described in this preparation. 

Durene (m.p. 79-80°), prepared according to the procedure in Org. Syn., Coll. Vol. 2, 248 (1943), was used by the submitter. Commercially available durene that also melted at 79—80° after purification by the Organic Syntheses procedure above was used by the checkers. 

This cyclopropane was prepared according to an organic Syntheses procedure, Org, Synth. 1985, 83, 147. 

According to a recent Organic Syntheses procedure, fluoromethyl phenyl sul-fone, which can be prepared on a large scale [90] (Eq. 23), undergoes a number of useful reactions. A Wadsworth-Emmons-type procedure affords a-fluoro-vinylsulfones [91], which undergo tin-sulfur exchange under free radical conditions (Eq. 24). The products maybe protodestannylated [92],fluorinated [93],or coupled under palladium catalysis [94]. The difluoromethyl phenyl sulfone also shows some useful chemistry. 

Chemists are invited to submit for publication in Organic Syntheses procedures for the preparation of compounds that are of general interest, as well as procedures that illustrate synthetic methods of general utility. It is fundamental to the usefulness of Organic Syntheses that submitted procedures represent optimum conditions, and the procedures should be checked carefully by the submitters, not only for yield and physical properties of the products, but also for any hazards that may be involved. Full details of all manipulations should be described, and the range of yield should be reported rather than the maximum yield obtainable by an operator who has had considerable experience with the preparation. For each solid product the melting-point range should be... 

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