Synthetic and Computational Studies of Silametacyclophanes: Macrocyclic Cage Compounds

dc.contributor.author Kwochka, William
dc.contributor.author Damrauer, Robert
dc.contributor.author Gordon, Mark
dc.contributor.author Schmidt, Michael
dc.contributor.author Gordon, Mark
dc.contributor.department Chemistry
dc.date 2018-02-17T07:38:35.000
dc.date.accessioned 2020-06-30T01:18:51Z
dc.date.available 2020-06-30T01:18:51Z
dc.date.copyright Sat Jan 01 00:00:00 UTC 1994
dc.date.issued 1994-09-01
dc.description.abstract <p>Multiple Pd(O)-catalyzed coupling reactions of9-borabicyclo[3.3.1]nonane (9-BBN) adducts of allylsilanes and bromo benzenes are used to prepare several unusual silametacyclophanes. Reaction of the 9-BBN adduct of dimethyldiallylsilane and 1,3-dibromobenzene gives 4-dimethyl-4-sila[7]metacyclophane in 32% yield, while reaction of the 9-BBN adduct of methyltriallylsilane and 1,3,5-tribromobenzene leads to 4-methyl-4-sila[34•10][7]metacyclophane in 4% yield. NMR data are presented to help characterize these compounds. Computational studies of the cyclophanes HE[-Y-(CH2)n-hCsH3 forE= C, Si, Y = CH2, 0, and n = 2, 3 reveal various important factors in stabilizing compounds with H atE inside the cage. These include that the macrocycle be large enough to accommodate the EH bond and that the EH bond be polarized so that its H atom is positive when directed toward the 1r cloud of the benzene ring. Even the small n = 2 macrocycles are only moderately strained at both E and the benzene base.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>Organometallics</em> 13 (1994): 3728, doi:<a href="http://dx.doi.org/10.1021/om00021a053" target="_blank">10.1021/om00021a053</a>. Copyright 1994 American Chemical Society.</p>
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dc.identifier archive/lib.dr.iastate.edu/chem_pubs/267/
dc.identifier.articleid 1263
dc.identifier.contextkey 7917984
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/267
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/14709
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/267/0-L_1994_Gordon_SyntheticComputational.pdf|||Fri Jan 14 23:03:46 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/267/1994_Gordon_SyntheticComputational.pdf|||Fri Jan 14 23:03:48 UTC 2022
dc.source.uri 10.1021/om00021a053
dc.subject.disciplines Chemistry
dc.title Synthetic and Computational Studies of Silametacyclophanes: Macrocyclic Cage Compounds
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 1a5927c0-5a5f-440e-86e0-9da8dc6afda0
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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