SYNTHESIS OF A NEW SYSTEM CONTAINING A PYRAMIDALIZED DOUBLE-BOND - CIS-3,8-DICARBOMETHOXY-3,8-DIHYDROHEPTALENE AND ITS REACTION WITH BENZYNE

MENZEK A., SARAÇOĞLU N., KRAWIEC M., WATSON W., BALCI M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.60, sa.4, ss.829-832, 1995 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 60 Sayı: 4
  • Basım Tarihi: 1995
  • Doi Numarası: 10.1021/jo00109a012
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.829-832
  • Ankara Üniversitesi Adresli: Hayır

Özet

The strained system syn-1 was the object of synthetic and structural studies because of its double bond pyramidalization. The starting material, cis-3, 8-dicarbomethoxy-3,8-dihydroheptalene, was synthesized by two different approaches. Addition of ethyl diazoacetate then gave syn-addition product 2. Transesterification and NBS-bromination followed by Zn-AcOH elimination resulted in the formation of cis-dihydroheptalene 5, which was also synthesized by silica gel catalyzed isomerization of the trans-5 isomer. Addition of benzyne to cis-5 gave the target compound syn-1, whose structure was investigated by X-ray diffraction. These data show its pyramidalization angle to be 16.8 degrees.