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Synthesis 1997; 1997(10): 1174-1178
DOI: 10.1055/s-1997-1324
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Preparation of 2-Zincio-1,3-Dithianes and Di(1,3-dithian-2-yl)zinc and Their Reaction with Highly Functionalized Halides and α,β-Unsaturated Carbonyl Compounds

Vanda Cerè1 , Silvia De Angelis1 , Salvatore Pollicino1 , Alfredo Ricci2 , Ch. Kishan Reddy3 , Paul Knochel3 , Gérard Cahiez4
  • 1Dipartimento di Chimica Organica “A. Mangini”, Via Risorgimento N°4, I-40136 Bologna, Italy
  • 2Dipartimento di Chimica Organica “A. Mangini”, Via Risorgimento N°4, I-40136 Bologna, Italy, Fax +39(51)6443654
  • 3Fachbereich Chemie der Phillips-Universität, Hans-Meerwein Strasse, D-35043 Marburg, Germany
  • 4Laboratoire de Chimie des Organoélements associé au CNRS, Université Pierre et Marie Curie, 4 Place Jussieu F-75252 Paris, France
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Publikationsdatum:
31. Dezember 2000 (online)

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The title compounds were obtained by simple transmetallation of the corresponding lithium derivatives with ZnCl2 or ZnBr2. Contrary to 2-lithio-1,3-dithianes, 2-zincio-1,3-dithianes can react with a number of electrophiles bearing reactive functional groups to afford highly substituted 1,3-dithianes in satisfactory to excellent yields. The synthesis of the new organozinc derivative, di(1,3-dithian-2-yl)zinc, which effectively adds to enones, is also reported.

2-zincio-1,3-dithianes - functionalized electrophiles - displacement reactions - addition reactions - selectivity