Bimane acetylenes and diacetylenes. Bimanes. 33

Edward M. Kosower; Marcia Ben-Shoshan

doi:10.1021/jo951830b

Bimane acetylenes and diacetylenes. Bimanes. 33

Edward M. Kosower^*, Marcia Ben-Shoshan

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	5871-5884
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	61
Issue number	17
DOIs	https://doi.org/10.1021/jo951830b
State	Published - 23 Aug 1996

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abstract = "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.",

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AB - 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.

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Bimane acetylenes and diacetylenes. Bimanes. 33

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