89229-02-7Relevant academic research and scientific papers
Generation and trapping of a highly strained bicyclic alkyne: Tricyclo[6.3.1.02,7]dodeca-2,4,6-trien-9-yne
Tuemer,Taskesenligil,Balci
, p. 3806 - 3810 (2007/10/03)
High-temperature bromination of 10-bromotricyclo[6.3.1.02,7] dodeca-2,4,6,9-tetraene (8) resulted mainly in the formation of two isomeric tribromides (16 and 17) whose dehydrobromination with DBU afforded the corresponding 9,10-dibromotricyclo [6.3.1.02,7] dodeca-2,4,6,9-tetraene (14). Treatment of 14 with tert-butyllithium in THF at -78 °C produces the strained bicyclic alkyne (10) which is trapped by 1,3-diphenylisobenzofuran to give two isomeric cycloadducts 12a and 12b. The adducts 12a and 12b were found to readily rearrange to the isomeric ketones 19a and 19b upon chromatography. Upon treatment with potassium tert-butoxide, the adducts 12a and 12b undergo base-catalyzed double bond isomerization to give four products 20-23. Furthermore, reaction of 14 with one and two mole of potassium tert-butoxide has been studied and the mechanism of the product formation is discussed with regard to either an allene or alkyne as a possible intermediate.
BICYCLIC ALLENES: GENERATION AND TRAPPING OF 6,7-BENZOBICYCLOOCTA-2,3-DIENE
Balci, Metin,Harmandar, Mansur
, p. 237 - 240 (2007/10/02)
Treatment of 3-bromo-6,7-benzobicycloocta-2,3-diene (9) with potassium tert.-butoxide produces the strained bicyclic allene (10) which is trapped by 1,3-diphenylbenzofuran (DBI) to give five isomeric cycloadducts.In the absence of DBI, allene (10) gave rise to enol ether (18) by addition of tert.-butanol.
