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On the Identity of Hofmann's “Dibenzyl-Phosphine” with Oxide of Tribenzyl-Phosphine, and on some other Points connected with the Phosphorised Derivations of Benzyl

Published online by Cambridge University Press:  15 September 2014

Letts  and
R. F. Blake
Letts
Affiliation:
Queen's College, Belfast
R. F. Blake
Affiliation:
Queen's College, Belfast
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Extract

In his well-known researches on the phosphines, Hofmann has shown (or believes that he has shown) that when an alkyl iodide (or other haloid derivative) is heated with phosphonium iodide and oxide of zinc, primary and secondary phosphines alone result; whereas, when an alcohol is heated with iodide of phosphonium, tertiary and quaternary phosphines are formed exclusively. Thus the two reactions are complementary to each other. Among the series to which he extended his investigations was that of benzyl, and in a paper published in the Berichte of the Berlin Chemical Society he describes the preparation of mono- and dibenzyl-phosphine, and gives their properties. Dibenzyl-phosphine he isolated as a crystalline substance perfectly tasteless and odourless, insoluble in ether, but soluble in alcohol. Its melting-point he found to be 205° C.

Type
Proceedings 1888-89
Information
Proceedings of the Royal Society of Edinburgh , Volume 16 , 1890 , pp. 193 - 200
Copyright
Copyright © Royal Society of Edinburgh 1889

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References

note * page 194 Berichte (1872), v. 100.Google Scholar

note * page 195 Details of this method will be given in another paper.

† It will be seen that a formula can be devised in every case, both for a compound of (C7H7)2HP and (C7H7)3PO, which corresponds with the results obtained; and it is remarkable how closely most of the results obtained agree with those required for a compound of the former. We also give in some cases the analyses of compounds prepared in a similar manner with what was known to be the oxide of tribenzyl-phosphine. Most of the compounds are unstable, and their composition often varies according to the method or conditions employed in their preparation.

note * page 198 We give this last formula partly because the first is improbable, and partly because the substance in question has the same melting-point and properties as the sulphide of tribenzyl-phosphine. But, on the other hand, we have not as yet detected sulphur in it, and unless that element was present in the crude products used, its occurrence is incomprehensible.