93756-84-4Relevant academic research and scientific papers
Organophosphorus Compounds, Part 168;1 1,3-Dipolar Cycloaddition Reactions of 1,3,5-Triphosphinines with Nitrile Oxides
Weidner, Steffen,Renner, Jens,Bergstraesser, Uwe,Regitz, Manfred,Heydt, Heinrich
, p. 241 - 248 (2007/10/03)
Phenylnitrile oxide as well as mesitylnitrile oxide underwent 1,3-dipolar cycloaddition reactions with the 1,3,5-triphosphinines 2 under mild conditions to furnish the condensed heterocyclic compounds 9 and 11, respectively. Oxadiphospholes 14 were accessible by fragmentation reactions of 11.
Unusually Coordinated Phosphorus Compounds; 22. Cycloaddition Reactions of Nitrilium Betaines with a Stable Phosphaalkyne
Roesch, W.,Regitz, M.
, p. 689 - 693 (2007/10/02)
(2,2-Dimethylpropylidyne)phosphane (7) undergoes regiospecific -cycloaddition reactions with the arylnitrile oxides 2a-c to yield the 1,2,4-oxazaphospholes 8a-c.In the reaction of phosphaalkyne 7 with 2,2-dimethylpropanenitrile oxide (2d) the 1:2-adduct 10 is formed in addition to 8d.The reaction of 7 with the nitrile sulphide 12 produces the 1,2,4-thiazaphosphole 13.The 1H-1,2,4-diazaphospholes 18a-c are obtained from the reactions of 7 with the nitrile imines 17a-c; the regioisomers 21a and 21b have been detected by NMR spectroscopy.
Phosphorus Compounds with Unusual Coordination, 5. - as well as -Cycloaddition Reactions to a Kinetically Stabilized Phosphaalkene
Zurmuehlen, Frank,Roesch, Wolfgang,Regitz, Manfred
, p. 1077 - 1086 (2007/10/02)
Aliphatic diazo compounds display different reactivity towards the phosphaalkene 9: diazomethane, diazoethane and tert-butyl diazoacetate (10a-c) formally react with Si/P-insertion to give the hitherto unknown phosphaalkenes 12a-c.In contrast, 1-diazo-2,2-dimethylpropane (10d) and diazotrimethylsilylmethane (10e) lead to the 1,2,4-diazaphospholes 15 and 17, respectively, if the primary products (11d, 14) are treated with sodium hydroxide in tetrahydrofuran.The reaction of the nitrile oxides 18a-c with 9 yields the 1,2,4-oxazaphospholes 20a-c; the cycloadducts 19a-c are assumed to occur as intermediates, which eliminate hexamethylsiloxane either spontaneously (19a, b) or with OH(-)-catalysis.Azide dipoles (21a-c) add to 9 with formation of 4,5-dihydro-1,2,3,4-phospholes (22a-c) which - instead of aromatization by hexamethyldisiloxane elimination - prefer fragmentation to 23 (-->25) and imidoesters 24a-c; hydrolysis produces the pivaloyl amides 26a-c.The 1:2 reaction between 9 and the o-quinones 31a-d proceeds via cycloadducts (32a-d) to produce the phosphoranes 34a-d by a subsequent cycloaddition process. - Key words: 1,3-Dipoles, o-Qiunones, Cycloaddition to a Phosphaalkene, Phospholes
