By Martin Windrow
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Extra info for Luftwaffe Colour Schemes and Markings 1935-45 vol 1
The reactions of acyltributylphosphonium ions (prepared in-situ from an 0 11 ph3bj\/P(OR)2 297 Me' Me + R3P-CHMe-SiMe2-S298 R=alkyl 299 R36-CHMe-SiMe&I CI- 300 acid chloride and tributylphosphine)with Grignard reagents provide a convenient, one-pot, route to ketonesM4. N-Substituted aminotriphenylphosphonium tribromides have been used for the regiospecific bromination of substituted phenols446. The triphenylphosphonium radical cation has been characterised by ESR techniques448. Donor-acceptor complexes have been obtained from combination of tetraphenylphosphonium chloride or bromide with iodobenzene in acetonitrile, which involve interaction of the halide ion of the salt with iodine.
Adducts of cyanomethylenetriphenylphosphorane with acyl-isocyanates and -thiocyanates undergo cyclisation with hydrogen chloride to form the salts 282, from which phosphonium betaines can be easily obtained4I4. , 283, have also been developed4153416. The reaction of the tributylphosphine - carbon disulfide adduct with norbornene has given the zwitterion 284, which, in solution, dissociates to form the ylide 285 from which 2alkylidene-l,3-dithiolanescan be formed417. , 287, can be prepared by alkylation or a ~ y l a t i o n ~Improved '~.
Sulfide 213 has been developed, and this can also be metallated and alkylated at the ~x-carbon~'~. The phosphine oxide 215 undergoes metallation ortho to the diphenylphosphinoyl group on 28 Organophosphorus Chemistry treatment with lithium tetramethylpiperidide. Subsequent iodination and Ullmanii coupling has given the biphenylic diphosphine dioxide 21(i3I8. g. (S)-bornyl or (1 R)-isopinocamphenyl 212 213 K, 0 214 215 216 Chiral phosphine oxides 217 have been obtained in high enantiomeric purity by treatment of diastereoisomeric carbohydrate esters of methyl(pheny1)phosphinic acid with a Grignard reagent319.