Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones

Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones

Bibliographic Details
Main Author: Zhang, Ming
Language:English
Published: Case Western Reserve University School of Graduate Studies / OhioLINK 2007
Subjects:
TMS
CYCLOPENTADIENONES
C6D6
9H
Hz
1H
Online Access:http://rave.ohiolink.edu/etdc/view?acc_num=case1164140647
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spelling ndltd-OhioLink-oai-etd.ohiolink.edu-case11641406472021-08-03T05:32:18Z Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones Zhang, Ming TMS CYCLOPENTADIENONES C6D6 9H Hz 1H The optimization of Fe(CO)5 promoted cyclocarbonylation of temporary silicon-tethered diynes is described. Various monomeric cyclopentadienones with hydroxyl substituents were produced in good yields as a result. Conjugate additions of carbon nucleophiles to these cyclopentadienones and their corresponding protected derivatives were studied. Chelate Mg coordinated cyclopentadienone intermediates were proposed to explain the resulting regio- and stereo-chemistry. For the mono-protected cyclopentadienone substrates, a hydroxyl-delivery mechanism was proposed. An unexpected cyclopropanation was observed during the conjugate additions of Grignard reagents to TBS protected hydroxyalkyl-substituted cyclopentadienones. It was prevented after replacing the TBS protecting group with methyl. 2007 English text Case Western Reserve University School of Graduate Studies / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=case1164140647 http://rave.ohiolink.edu/etdc/view?acc_num=case1164140647 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws.
collection NDLTD
language English
sources NDLTD
topic TMS
CYCLOPENTADIENONES
C6D6
9H
Hz
1H
spellingShingle TMS
CYCLOPENTADIENONES
C6D6
9H
Hz
1H
Zhang, Ming
Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
author Zhang, Ming
author_facet Zhang, Ming
author_sort Zhang, Ming
title Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
title_short Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
title_full Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
title_fullStr Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
title_full_unstemmed Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones
title_sort conjugate additions of carbon nucleophiles to cyclopentadienones
publisher Case Western Reserve University School of Graduate Studies / OhioLINK
publishDate 2007
url http://rave.ohiolink.edu/etdc/view?acc_num=case1164140647
work_keys_str_mv AT zhangming conjugateadditionsofcarbonnucleophilestocyclopentadienones
_version_ 1719421432088231936

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