✦ LIBER ✦

Arsirane synthesis by reaction of sulfur ylides with diazaarsoles

✍ Scribed by Souad Himdi- Kabbab; Jack Hamelin

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 168 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97311-8

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✦ Synopsis

m : N-unsubstituted diazaarsoles 4 undergo an N alkylation by reaction with sulfur yliaks. N-substituted diazaarsoles 5. and 2 react with dimethylsulfoxonium ylide to give stable bicyclic arsiranei u and 12. Aziridines are well known precursors of azomethine ylides and we wondered if arsimnes could behave in the same way to give the corresponding arsenic 1,3 dipole according to the following scheme : X=N X=As? 13C NMR : 14.27 (2q. CHW) ; 52.86 (2d, As-m-C) ; 61.46 (t, aCH3) ; 62.19 (s. carbon) ; 70.59 (d, Phm quaternary ; 128.12 ; 128.55 ; 129.04 et 139.43 (m, Ph2C) ; 178.56 (s, C=N) ; 163.02 and 164.24 (2s, 2C=G). Mass Spectrometry : (M+ -CI-I2) C2lH2lN204As : calculated : 440.07171 ; found : 440.0728. molecular ion m/z = 454 is not seen. Elementary analysis : C22H23N204As : calculated % C 58.14 H 5.06 N 6.16 found 57.47 4.73 6.19 10. 12 (F = 61'C) IH NMR (CDCl3, Lock TMS) : 1.42 (t, 6H, CI-I-) ; 3.92 (s, 2H, As-CH2-C) ; 4.40 (m, COaCH3) ; 4.5 (s, NCH3).

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