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Ortho-substitution of the benzene ring in 3-arylsydnones mediated by butyllithium

✍ Scribed by S. T. Lin; H. S. Cheo; B. I. Chen; Z. Y. Own

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 142 KB
Volume: 9
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1998)9:6<549::aid-hc4>3.0.co;2-#

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✦ Synopsis

C(4), CЈ(2)-Double substitution was achieved in good yields by reacting 3-arylsydnones with BuLi and then with a suitable electrophile in THF at ‫05מ‬ЊC. ᭧ 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:549-552, 1998 1 H NMR d 7.41-7.52 (m, 20H, Ar-H), 7.76-7.84 (m, 3H, Ar-H); IR 1723 (m CO ) cm ‫1מ‬ ; MS m/z (%) 575 (M ‫ם‬ , 1), 376 (100); anal. calcd for C 32 H 23 N 3 O 4 P 2 : C, 66.79; H, 4.03; N, 7.30. Found: C, 66.75; H, 4.09; N, 7.24. Chloro-di-(tert-butyl )phosphine. 4-(Di-(tert-butyl)phosphino)-3-(4-nitrophenyl)sydnone 17: yield 76%; mp 157-159ЊC; 1 H NMR d 1.37 (s, 9H, 3 ‫ן‬ CH 3 ), 1.44 (s, 9H, 3 ‫ן‬ CH 3 ), 7.94 (d, 2H, J ‫ס‬ 9.5 Hz), 8.52 (d, 2H, J ‫ס‬ 9.5 Hz); IR 1756 (m CO ) cm ‫1מ‬ ; MS m/z (%) 351 (M ‫ם‬ ‫מ‬C 4 H 8 , 5), 57 (100); anal. calcd for C 16 H 22 N 3 O 4 P: C, 54.70; H, 6.

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