Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization

9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disila­anthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was signif...

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Bibliographic Details
Published inOrganometallics Vol. 32; no. 7; pp. 2092 - 2098
Main Authors Kuribara, Takayoshi, Ishida, Shintaro, Kudo, Takako, Kyushin, Soichiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.04.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
BERRY PSEUDOROTATION
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Summary:9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disila­anthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si–H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.
Bibliography:KAKEN
ISSN:0276-7333
1520-6041
DOI:10.1021/om301170r