Compounds containing carbon–phosphorus bonds

Abstract

PHOSPHORUS-CONTAINING organic compounds present a variety of features of chemical interest. Many complex esters and amides of phosphoric and condensed phosphoric acids play important parts in metabolic processes, but compounds whose molecules contain carbon atoms linked directly to phosphorus do not occur naturally. They are discussed, together with other organic compounds of phosphorus, in Kosolapoff's book which summarises the literature up to the beginning of 1950 and is a mine of information for all workers in this field. It is usefully supplemented by a recent review 2 dealing with the preparation and properties of phosphonic acids, the most important class of compounds containing C-P bonds, Although phosphorus follows nitrogen in Group V of the Periodic Table there is very little resemblance between the organic chemistry of these two elements. Phosphorus analogues of important classes of organic nitrogen compounds such as nitro-compounds, aromatic nitrogen-heterocycles and azo-compounds are mostly unknown and where formal similarities do exist , as between primary phosphines and primary amines or between phosphine oxides and amine oxides, there are considerable differences in reactions.These dissimilarities arise because of the lower electronegativity of phosphorus which leads to its forming stronger bonds with oxygen and with halogens, and because of the greater reactivity of the unshared electrons on tervalent phosphorus which results in a strong tendency to quinquevalency. Nomenclature of OrganicCompounds of Phosphorus.-The problem of providing suitable, unambiguous names for organic phosphorus compounds is one which has caused considerable difficulty. The majority of organic phosphorus compounds can be considered as derived from various acids of phosphorus; the existence of two valency states and of both mono-and di-basic acids, together with the problem of whether negative substituents such as chlorine or amino-groups should be considered as replacing hydrogen or hydroxyl in the parent structure, led to several different systems of nomenclature. The resulting confusion was dispelled as far as British and American publications are concerned by the adoption in 1952 by the Chemical Society and the American Chemical Society of a new system of nomenclature for compounds containing one phosphorus atom.3 This system uses, as parent structures, a number of phosphorus hydrides and acids, some of which exist only hypothetically. I n naming compounds, groups which are attached by C-P bonds are considered as replacing hydrogen

The Behaviour of 1,2,3-Indantrione Towards Wittig-Horner Reagents

“…All melting points are uncorrected. Wittig-Horner reagents 1a-d were prepared by the Michaelis-Arbuzov reaction [ 12 , 13 ]. Cyanomethylenetriphenylphosphorane was prepared by a published procedure [ 14 ].…”

The Reaction of Wittig and Wittig-Horner Reagents and Alkyl Phosphites with 1,2-Naphthoquinone-1-benzimide

“…Carbomethoxymethylene and carbethoxymethylene triphenylphosphoranes were prepared according to established methods [15]. Trimethyl and triethyl phosphonoacetates were prepared by Michaelis-Arbuzov reactions [16,17]. Alkyl phosphites were prepared according to known procedures and puri®ed by fractional distillation [18,19].…”

Chemotherapy of Viral Infections

“…Compounds with carbon-phosphorous bonds are rare in nature (CROFTS 1958) and have not been extensively investigated for biologic activity. Compounds with carbon-phosphorous bonds are rare in nature (CROFTS 1958) and have not been extensively investigated for biologic activity.…”