Attempted synthesis of a highly strained bicyclic alkyne: Reaction of 8-chloro-6,9-dihydro-5,9-methano-5H-benzocycloheptene with potassium t-butoxide and an anomalous substitution reaction at a vinyl system
Özet
Treatment of alkene (9) with N-bromosuccinimide gave a mixture of monobromides [(10) and (11)] which were hydrolysed to the corresponding exo alcohol (13). Oxidation of (13) and subsequent hydrogenation of unsaturated ketone (14) afforded the ketone (15). Ketone (15) was treated with PCl5, followed by potassium t-butoxide to give chloro alkene (8b). Reaction of (8b) with potassium t-butoxide resulted in the formation of unexpected allyl ether (18) whose formation mechanism has already been discussed.
Atıf için künye
TÜMER, F., Taşkesenligil, Y., Daştan, A., & BALCI, M. (1996). Attempted synthesis of a highly strained bicyclic alkyne: Reaction of 8-chloro-6,9-dihydro-5,9-methano-5H-benzocycloheptene with potassium t-butoxide and an anomalous substitution reaction at a vinyl system. AUSTRALIAN JOURNAL OF CHEMISTRY, 49(5), 599–603. https://doi.org/10.1071/ch9960599
BibTeX
@article{tumer1996-70691,
author = {TÜMER, Ferhan and Taşkesenligil, Yavuz and Daştan, Arif and BALCI, Metin},
title = {Attempted synthesis of a highly strained bicyclic alkyne: Reaction of 8-chloro-6,9-dihydro-5,9-methano-5H-benzocycloheptene with potassium t-butoxide and an anomalous substitution reaction at a vinyl system},
journal = {AUSTRALIAN JOURNAL OF CHEMISTRY},
year = {1996},
volume = {49},
number = {5},
pages = {599--603},
issn = {0004-9425},
doi = {10.1071/ch9960599},
url = {https://akademik.atauni.edu.tr/yayinlar/70691-attempted-synthesis-of-a-highly-strained-bicyclic-alkyne-reaction-of-8-chloro-69}
}