Two series (4,6-dihydro and 4,6-dimethyl) of syn-bimanes [1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones] have been converted to acetylene and diacetylene derivatives. Their chemical and photophysical properties are reported. The 3-(and 6-)iodo (diiodo) derivatives are the best choices for Stille or Heck condensations with acetylenes or acrylates. Desilylation of (trimethylsilyl)acetylenes is best carried out with silver nitrate followed by lithium bromide. The acetylenes and diacetylenes are quite stable and highly fluorescent and represent candidate units for incorporation into polymers.
Bimanes. 14. Synthesis and properties of 4,6-bis(carbalkoxy)-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones [4,6-bis(carbalkoxy)-9,10-dioxa-syn-bimanes]. Preparation of the parent syn-bimane, syn-(hydrogen,hydrogen)bimane
作者:Edward M. Kosower、Dov Faust、Marcia Ben-Shoshan、Israel Goldberg
DOI:10.1021/jo00341a007
日期:1982.1
KOSOWER, E. M.;FAUST, D.;BEN-SHOSHAN, M.;GOLDBERG, I., J. ORG. CHEM., 1982, 47, N 2, 214-221
作者:KOSOWER, E. M.、FAUST, D.、BEN-SHOSHAN, M.、GOLDBERG, I.