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Siloxy-cope rearrangements of the trans-l-vinylcyclotridec-3-en-l-ol system

Creator:: Bolesta, Richard Edward
Abstract:: The thermolysis of trans-1 -trimethylsiloxy- 1-vinylcyclotridec- 3-ene (VI-OTMS) led to the formation of two major products: 4-vinylcyclotridecanone (VII) and cyclopentadec-5-en-l-one (VIII) after hydrolysis. Ketone VII is produced by a concerted [3, 3] sigmatropic shift, while ketone VIII is formed by a [1, 3] sigmatropic shift with a concerted or diradical...
Resource Type:: Masters Thesis
Full Text:: AN ABSTRACT OF THE THESIS OF RICHARD EDWARD BOLESTA for the

Oxy-Cope, and Siloxy-Cope rearrangement of cis-1-vinylcyclooct-3-en-1-ol

Creator:: Chin, Alice Wai-lee
Abstract:: Both oxy-Cope and siloxy-Cope rearrangements involve (1, 3) and (3, 3) sigrnatropic shifts. Both the concerted mechanism, and the stepwise mechanism via a diradical intermediate are possible. In a cyclic system such as cis-l-vinylcyclooct-3-en-l-ol, the thermal rearrangement takes place preferably through a diradical intermediate. At high temperature, the reaction also...
Resource Type:: Masters Thesis
Full Text:: Rearrangement of cis-l-vinyl- cyclooc t-3 -en -I .ol, Abstract approved: Redacted for Privacy Dr. Richard W

A pyrolysis of cis-1-trimethylsiloxy-1-cyclopropyl-3-cyclononene : the thermal isomerization of 2-phenyl-1-trimethylsiloxy-1-vinylcyclononane

Creator:: Choi, Young Bok
Abstract:: Part 1 The pyrolysis of cis-1-trimethylsiloxy-1-cyclopr opyl-3-cyclononene in the temperature range 285-350° is described. Instead of siloxy-Cope rearrangement, undesired desiloxylation took place. Part 2 Gas-phase pyrolytic rearrangement of 2-phenyl-1-trimethylsiloxy-1-vinylcyclononane was investigated in a static system in the temperature range 213-330°. It was discovered that three major products resulted: cis- and...
Resource Type:: Masters Thesis
Full Text:: Redacted for privacy Dr. Richard W. Thies The pyrolysis of cis -1 tr imethyls iloxy- 1 - cyclopr opyl- 3

Exploratory studies of the mechanism of 1,3 sigmatropic ring expansion reactions

Creator:: James, Corinne Patricia
Abstract:: The potassium salts of certain 1-vinylcycloalk-3-en-l-ols have been found to undergo sigmatropic ring expansion rearrangements in HMPA. Preliminary investigations of several benzo-substituted medium ring systems were undertaken in order to determine which of these was best suited for further study. A synthetic sequence leading to the formation of 5-methy1-6-viny1-7,8,9,10-tetrahydro-6-benzocyclo-octenol, which...
Resource Type:: Masters Thesis
Full Text:: Sigmatropic Ring Expansion Reactions Abstract approved: Redacted for Privacy Richard W. Thies The potassium

Oxymercuration of cyclodeca-1,2,5,8-tetraene

Creator:: Hong, Pak-Kong
Abstract:: The reactions of cyclodeca-1, 2, 5, 8-tetraene with mercuric salts in solvents of varying nucleophilicity are described. Instead of forming the usual oxymercuration products reported for reactions of olefins and allenes with mercuric salts, the major products obtained in the present cases result from the initial electrophilic addition of the...
Resource Type:: Masters Thesis
Full Text:: CYCLODECA-1, 2, 5, 8-TETRAENE Abstract approved: Redacted for privacy Dr. Richard W. Thies The reactions

Ring expansion 3-methoxy-6-vinyl-7,8,9,10-tetrahydro-6(5H)-benzocyclooctenol

Creator:: Meshgini, Mehdi
Resource Type:: Masters Thesis
Full Text:: )-BENZOCYCLOOCTENOL Abstract approved: Redacted for Privacy Dr. Richard W. Thies The potassium salts of 6- vinyl -7

Catalytic rearrangement of cyclodeca-1,2,5-triene and oxymercuration of bicyclo-[7.1.0]-deca-2,3-diene

Creator:: Boop, Janice Lee
Abstract:: The reaction of cyclodeca-1,215triene with mercuric salts gave only rearranged hydrocarbon, tricyclo[4.4.0.0²'⁴]deca-5ene in acetic acid. Other catalysts [Rh(CO)₂C1]₂ and AgC10₄ gave the same rearranged hydrocarbon. The isomerization is proposed to proceed through a "metalcomplexed" carbenoid intermediate. The reaction of bicyclo[7.1.0 ]deca-213diene gave oxymercurated products.
Resource Type:: Masters Thesis
Full Text:: for Privacy Dr. Richard W. Thies The reaction of cyclodeca-1,215triene with mercuric salts gave

The siloxy-cope rearrangement of 1,2-divinyl-1-trimethyl-siloxycyclohexane and related systems. The acid-catalyzed rearrangement of bicyclo [5.1.0] octyl-8-methanol

Creator:: Walton, Edward Samuel
Abstract:: Part I The pyrolysis of cis- and trans- 1, 2-divinyl-1- trimethylsiloxy - cyclohexane, II- and III-TMS, under the same conditions as the pyrolysis of cis-l-vinyl -1-trimethylsiloxycyclooct-3-ene, I-TMS, confirms that a sequence of concerted reactions for the rearrangement of II- and III-TMS to trans-l-trimethylsiloxycyclodec-3-ene, IV-TMS, is a viable pathway in the...
Resource Type:: Masters Thesis
Full Text:: approved: Part I Redacted for Privacy Dr. Richard W. Thies The pyrolysis of cis- and trans- 1, 2-divinyl

Syntheses of large ring hormone analogs

Creator:: Yue, Stephen T.
Abstract:: The (±) 8,9:13,14-diseco-norestradiol, a large ring hormone analog, and its related derivatives, were prepared by a ring expansion approach. The key step of this approach is the establishment of the benzocyclododecenone system via the Caubere reaction. This step not only provides a favorable ring size, it also sets the necessary...
Resource Type:: Dissertation
Full Text:: : SYNTHESES OF LARGE RING HORMONE ANALOGS Abstract approved: _Redacted for privacy Richard W. Thies The

Siloxy-cope and oxy-cope rearrangements of the cis- and trans-1-vinylcyclodec-3-en-1-ol systems ; Acid-catalyzed rearrangement of cis-bicyclo [6.1.0] nonane-cis- and trans-9-methanols ; An effective two-carbon ring-expansion

Creator:: Billigmeier, James Earl
Resource Type:: Dissertation
Full Text:: Redacted for privacy Dr. Richard W. Thies The thermal rearrangements of trans-l-vinylcyclodec-3-en-l-ol

ScholarsArchive@OSU

Siloxy-cope rearrangements of the trans-l-vinylcyclotridec-3-en-l-ol system

Oxy-Cope, and Siloxy-Cope rearrangement of cis-1-vinylcyclooct-3-en-1-ol

A pyrolysis of cis-1-trimethylsiloxy-1-cyclopropyl-3-cyclononene : the thermal isomerization of 2-phenyl-1-trimethylsiloxy-1-vinylcyclononane

Exploratory studies of the mechanism of 1,3 sigmatropic ring expansion reactions

Oxymercuration of cyclodeca-1,2,5,8-tetraene

Ring expansion 3-methoxy-6-vinyl-7,8,9,10-tetrahydro-6(5H)-benzocyclooctenol

Catalytic rearrangement of cyclodeca-1,2,5-triene and oxymercuration of bicyclo-[7.1.0]-deca-2,3-diene

The siloxy-cope rearrangement of 1,2-divinyl-1-trimethyl-siloxycyclohexane and related systems. The acid-catalyzed rearrangement of bicyclo [5.1.0] octyl-8-methanol

Syntheses of large ring hormone analogs

Siloxy-cope and oxy-cope rearrangements of the cis- and trans-1-vinylcyclodec-3-en-1-ol systems ; Acid-catalyzed rearrangement of cis-bicyclo [6.1.0] nonane-cis- and trans-9-methanols ; An effective two-carbon ring-expansion

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