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By M.J.Kamlet, S.J.Jacobs

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The CNO group is almost linear. The atomic distances in formonitrile oxide (fulminic acid) in relation to th~ coordinate system, and those of 4-methoxy-2,6-dimethylbenzonitrile oxide are depicted in formulas 1 and 2. 2633 ---~ 30 Physical Properties CR, 2 (distances in A) distance for the N-o- 'bond in both compounds. As a result from the various cited studies and theoretical calculations the resonance interaction ofthe two kinds of n systems (n and it) has been represented by Fig. 1. Fig. 1. Scheme of it-resonance interaction in benzonitrile oxide 2 III.

Ann. Chern. 505, 237 (1933). 32 Preparation suitable for the preparation of the higher homologs. , metal salts, amides, O-esters) for which no analogs exist among the other nitrile oxides. A table of all individual nitrile oxides prepared by the methods discussed in the following sections of this chapter is provided in Chapter II, pp. 16-20. Formonitrile Oxide (Fulminic Acid) and Derivatives 33 B. Formonitrile Oxide (Fulminic Acid) and Derivatives Because of its instability, fulminic acid (6) has always been prepared first in form of its mercuric or silver salts.

Ber. 28,1213 (1895); 35,151 (1902); 39, 784 (1906). : Ann. Chern. 400, 302 (1913). From Aldoximes 49 acid halides 13. ) directly in the dehydrochlorination reaction (Eq. (6)) produced nitrile oxides in moderate to good yields (40-60%), while the isolation of a crystalline constant melting 13 gave an essentially quantitative yield of the nitrile oxide. This has been interpreted as an indication that only one stereoisomer is capable of neat nitrile oxide formation. If it is permissible to draw analogies to the dehydrogenation of aldoximes (see preceding paragraph) one would assume that it is the syn isomer of 13 which provides the nitrile oxide.

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