Abstract
The synthesis of crowded peri-5-bromo-6-(organostannyl)acenaphthenes is described. Reaction of 5,6-dibromoacenaphthene with 1 equiv of n-BuLi at −40 °C in diethyl ether followed by addition of the appropriate organotin reagent at 0 °C gave 5-bromo-6-(triphenylstannyl)acenaphthene (1), 5-bromo-6-(chlorodiphenylstannyl)acenaphthene (2), bis(6-bromoacenaphthen-5-yl)diphenylstannane (3), bis(6-bromoacenaphthen-5-yl)dibenzylstannane (4), bis(6-bromoacenaphthen-5-yl)dibutylstannane (6), and bis(6-bromoacenaphthen-5-yl)dichlorostannane (7) in low to medium yields (10–56%). 4 was converted into 5-iodo-6-bromoacenaphthene (5) by stirring overnight in the presence of a large excess of iodine. The new compounds were fully characterized spectroscopically. 119Sn NMR spectra suggest and interaction between the tin atoms and the neighboring peri halogen atoms. Single-crystal X-ray studies on 1–4 and 6–8 revealed Sn···X distances which are significantly less than the sum of the van der Waals radii, while DFT calculations...
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
