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The reactivity of stable metallacycl...

Holland, Ryan Lynn.

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The reactivity of stable metallacyclobutenes and vinylcarbenes.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	The reactivity of stable metallacyclobutenes and vinylcarbenes./
作者:	Holland, Ryan Lynn.
面頁冊數:	305 p.
附註:	Source: Dissertation Abstracts International, Volume: 77-10(E), Section: B.
Contained By:	Dissertation Abstracts International77-10B(E).
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10128435
ISBN:	9781339864471

The reactivity of stable metallacyclobutenes and vinylcarbenes.
Holland, Ryan Lynn.

The reactivity of stable metallacyclobutenes and vinylcarbenes. - 305 p.

Source: Dissertation Abstracts International, Volume: 77-10(E), Section: B.

Thesis (Ph.D.)--University of California, San Diego, 2016.

Chapter 1. Historical Development of Stable Metallacyclobutenes: Fred Tebbe and co-workers synthesized the first stable metallacyclobutene complexes in the late 1970's by treatment of an intermediate titanium methylene species -- later popularized as the "Tebbe reagent" -- with acetylenes. Robert Grubbs at Caltech further studied this system, using it to detail a degenerate metathesis reaction and to isolate a metallacyclobutane complex -- which was implicated in the emerging field of alkene metathesis. Further development of stable metallacyclobutene complexes is explored chronologically, particularly with regard to systems developed by Thorn, Bianchini, Hughes, O'Connor, Casey, Wojcicki, and Chen.

ISBN: 9781339864471Subjects--Topical Terms:

523952
Organic chemistry.

The reactivity of stable metallacyclobutenes and vinylcarbenes.
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245 1 4 $a The reactivity of stable metallacyclobutenes and vinylcarbenes.
300 $a 305 p.
500 $a Source: Dissertation Abstracts International, Volume: 77-10(E), Section: B.
500 $a Adviser: Joseph M. O'Connor.
502 $a Thesis (Ph.D.)--University of California, San Diego, 2016.
520 $a Chapter 1. Historical Development of Stable Metallacyclobutenes: Fred Tebbe and co-workers synthesized the first stable metallacyclobutene complexes in the late 1970's by treatment of an intermediate titanium methylene species -- later popularized as the "Tebbe reagent" -- with acetylenes. Robert Grubbs at Caltech further studied this system, using it to detail a degenerate metathesis reaction and to isolate a metallacyclobutane complex -- which was implicated in the emerging field of alkene metathesis. Further development of stable metallacyclobutene complexes is explored chronologically, particularly with regard to systems developed by Thorn, Bianchini, Hughes, O'Connor, Casey, Wojcicki, and Chen.
520 $a Chapter 2. Reactivity of Stable Metallacyclobutenes and Vinylcarbenes with Alkenes: Cobalt-metallacyclobutene complex (eta5-C5H5)(PPh3)Co[kappa2-(C,C)-C(SO2Ph)=C(TMS)CH(CO2Et)] is allowed to react with a variety of acyclic and cyclic alkenes to generate stable eta4-1,4-pentadienes (9-12) and kappa2-metallacyclohexenes (13-14), respectively. The reaction is thought to occur through a vinylcarbene intermediate such as 15-17, and a model complex of an oxametallabenzene containing an internal vinylcarbene moiety is calculated (18). Complex 13-exo reacts with trimethylphosphine to decomplex the ester carbonyl, generating a PMe3 complex, 20-exo. Oxidative demetallation of complexes 9-ZZ and 9-ZE is effected with iodine to generate organic pentadienes 21-22. Iron vinylcarbene complex (CO)3Fe(eta3-C(OMe)C(CO2Me)=CH(CO2Me) (25a) is synthesized, and its reactivity with maleic anhydride and maleimide is found to generate dinuclear iron complex 30, and new organic species 31 and 32. Compounds 31-32 are formulated as the [4 + 2]-cycloaddition product of an intermediate furan or alpha-pyrone.
520 $a Chapter 3. Reactivity of Stable Metallacyclobutenes with C-Nitroso Reagents: Cobaltacyclobutene complex (eta5-C5H5)(PPh3)Co[kappa2-(C,C)-C(SO2Ph)=C(TMS)CH(CO2Et)] is found to react with C-nitroso reagents to afford bicyclic [kappa2-(C,O)-eta1-(N)-hydroxylamido complexes 5-9. Complexes 5-9 contain a [3.1.0] fused-ring framework, with the 3-membered oxametallaziridine moiety formed in either a cis or trans relationship to the ethyl ester. Formation of products 5-9 is proposed to occur through a [4 + 2]-cycloaddition mechanism from an oxametallabenzene, with stereo-selection via rapid epimerization of nitrogen from the post-cyclization intermediate.
520 $a Chapter 4. The Isolation of a Large Cyclopentadienylcobaltsulfide Cluster -- Synthesis and Crystal Structure of Octahedral closo-[(eta5-C5H5)Co]5S: The metallacyclobutene complex (eta5-C5H5)(PPh3)Co[kappa2-(C,C)-C(SO2Ph)=C(TMS)CH(CO2Et)] reacts with added (eta5-C5H5)Co(PPh3)2 to give the cluster compound closo-[(eta5-C5H5)Co]5S (1), the largest (eta5-C5H5)Co cluster known.
590 $a School code: 0033.
650 4 $a Organic chemistry. $3 523952
650 4 $a Inorganic chemistry. $3 3173556
690 $a 0490
690 $a 0488
710 2 $a University of California, San Diego. $b Chemistry. $3 1023460
773 0 $t Dissertation Abstracts International $g 77-10B(E).
790 $a 0033
791 $a Ph.D.
792 $a 2016
793 $a English
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