Article abstract of DOI:10.1080/10426509608046368

The reaction of N-methyl-N-trimethylsilylaminomethyl-dimethy]phosphine 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 trimetnylsilyl group, failed. 13 was allowed to react with two different acyl chlorides in the presence of tri-ethylamine 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=PMe₂ group.

Full text of DOI:10.1080/10426509608046368

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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DARSTELLUNG VON PEPTOIDEN
MIT DER ORGANOAMINOMETHYL-
DIMETHYLPHOSPHINOXID-GRUPPIERUNG
Thomas Kaukorat a , Ion Neda a , Peter G. Jones a & Reinhard
Schmutzler a
a Institut für Anorganische und Analytische Chemie der Technischen
Universität , Postfach 3329, 38023, Braunschweig, Germany
Published online: 04 Oct 2006.
To cite this article: Thomas Kaukorat , Ion Neda , Peter G. Jones & Reinhard Schmutzler (1996)
DARSTELLUNG VON PEPTOIDEN MIT DER ORGANOAMINOMETHYL-DIMETHYLPHOSPHINOXID-
GRUPPIERUNG, Phosphorus, Sulfur, and Silicon and the Related Elements, 112:1-4, 247-259, DOI:
10.1080/10426509608046368
To link to this article: http://dx.doi.org/10.1080/10426509608046368
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