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Abstract
The reaction of N-methyl-N-trimethylsilylaminomethyl-dimethylphosphine oxide 1 with various acyl chlorides furnished, in good yield, a series of phosphorus-containing peptoids, 2–10, bearing the dimethyl dimethylphosphino group. All compounds show similar n.m.r. spectra, except 10, involving the 2,2,2-trichloro-tert.-butoxy substituent at nitrogen. In this case, doubling of the n.m.r. resonances is rationalized by assuming two geometric isomers (E/Z isomers). Similar results were observed for the corresponding thiophosphoryl compound 12. The reaction of dimethylphosphine oxide with hexahydro-1,3,5-tribenzyl-s-triazine led to 13, which is analogous to 1, with hydrogen and a benzyl group bonded to nitrogen. Attempts to react 13 with diethylaminotrimethylsilane, in order to substitute hydrogen by the trimethylsilyl group, failed. 13 was allowed to react with two different acyl chlorides in the presence of triethylamine as a base to form the phosphorus-substituted peptoids, 15 and 16 in good yields. X-ray crystal structure determinations were conducted for 2, 7, 8 and 16. The molecular backbone displays virtually constant configuration except for the O[tbnd]PMe2 group.
