ISSN:
1434-4475
Keywords:
Sila-Perfumes
;
Isosteric compounds
;
Theory of smell
;
Phosphinimides
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Zusammenfassung Derivatives of benzyldialkylphosphinimides C6H5CH2-PRR′=NH (C) with =NCH3, =NSiMe 3, =O, =S, −CS 2 ⊖ and −NH2]NCS⊖ instead of =NH groups (compare Scheme 1) were prepared and characterized. They neither show the H/D exchange of CH2 benzyl protons with CDCl3 nor the thermal formation of stilbene on heating like the parent compounds C, but they give in the case of =NCH3 and =NSiMe 3 analogously aHorner-Wittig reaction with aldehydes. CS2 reacts with C under NH/S-exchange. The quality of smell ofPhCH2-PRR′ =NCH3 (none, later fishy) is quite different from that of isostericPhCH2-SiRR′ −OCH3 (flowery-honeylike/minty) and the smell of C (metallic/chlorinated hydrocarbon-like) from that ofGrimm hydride isostersPhCH2−PRR′=O (weak; flowery-waxy). The theory ofAmoore (size and shape of molecules control their smell qualities) must be called in question.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00798274
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