Chemistry of Heterocyclic Compounds: The Heterocyclic

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Extra resources for Chemistry of Heterocyclic Compounds: The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, Volume 1

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P. 27). p. p. 5' (Quin, Peters, Griffin, and Gordon39). Details of the pmr spectra of these compounds in deuteriochloroforrii solubion are given t o illustrate the distinction between 2- and 3-phospholenes. 2 cps ( 2 vinyleiie protons). These show that (29) must hnvo the 3-phospholene structure, for the 2-phospholene structure would hnvo two-nonequivalent CH2 groups and t w o non-equivalent vinylene protons. J 14cps (3methylprotons); ~ 5 . 18 ppm, J 36 cps (2 vinylene protons). 5 cps ( 2 vinylene protons).

P. 161-163";this did not undergo EL Wittig reaction with cyclohexanone. p. 5", identified by its nmr spectrum aa 2-methyl-1,2,5-triphenyl-3-phospholene l-oxide (a), which, it is suggested, arose from the unstable three-membered ring system (42) ; catalytic hydrogenation of (43) gave the corresponding phospholane. The products formed by the action of the triphenylphosphole and its 1-oxide with methyl diazoacetate varied considerably with the conditions. (a)The phospholc in boiling dioxan containing copper powder gave the dimebhyl ester (39), presumably by intermediate decomposition of the diazoacetate to dimethyl fumarate.

1,2,3,4-tetrahydro-1 ,2,2,3,4,4-hexamethylphosphinolirie 1-oxide (cf. I,. 124). p. p. 108-120" (81%). * 12 Part I Cremer ‘Ja has later reinvestigated the alkaline hydrolysis of 1,2,2,3,4,&hexamethyl-1 -phenylphosphetanium bromide, and by deuterium labelling has reaffirmed the formation of the phosphine oxide (18): rearrangement of this oxide t o the substituted phosphinoline oxide (29) presumably occurs during the aromatization process in boiling decalin. 1 g of dichloride) and the acid, isolated by evaporation of the final solution, was identified solely by a phosphorus analysis, its identity must remain uncertain.

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