〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes

碩士 === 輔仁大學 === 化學系 === 94 === 1-Bromo-2-phenylcyclopropene (55) was synthesized by treating 1,1,2- tribromo-2-phenylcyclopropane 52 with 1 eq. methyllithium. Cyclopropene (55) underwent [2+2] dimerization to give 1,2-dibromo-4,5-diphenyl- tricycle[3.1.0.02,4]hexane (57). When 57 was heated at tolue...

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Main Authors: JIANG SHI-FEN, 江詩芬
Other Authors: LEE GON-ANN
Format: Others
Language:zh-TW
Published: 2005
Online Access:http://ndltd.ncl.edu.tw/handle/28893733061734407100
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spelling ndltd-TW-094FJU000650132015-10-13T10:38:05Z http://ndltd.ncl.edu.tw/handle/28893733061734407100 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes 環丙烯之〔2+2〕環化加成反應 JIANG SHI-FEN 江詩芬 碩士 輔仁大學 化學系 94 1-Bromo-2-phenylcyclopropene (55) was synthesized by treating 1,1,2- tribromo-2-phenylcyclopropane 52 with 1 eq. methyllithium. Cyclopropene (55) underwent [2+2] dimerization to give 1,2-dibromo-4,5-diphenyl- tricycle[3.1.0.02,4]hexane (57). When 57 was heated at toluene refluxing temperature, 1,2-dibromo4,5-diphenyl-1,4-cyclohexadiene (58) and 1,2- dibromo-4,5-diphenylbenzene (59) were obtained. Compound 58 could be oxidated to yield 59. Both 1-phenylcyclopropene and 55 can proceed [2+2] dimerization, therefore we could use the same character to get the crossed [2+2] cycloaddition adduct 1-bromo-2-hydrogen-4,5-diphenyltricyclo[3.1.0.02,4]- hexane 62. This is the first confirmed crossed [2+2] cycloaddition of cyclopropenes. When the adduct 62 was heated at toluene refluxing temperature for 5 hours, 1-bromo-4,5-diphenyl-1,4-cyclohexadiene (63) and 1-bromo-4,5-diphenylbenzene (64) were received. Compound 63 could be oxidated to yield 64. LEE GON-ANN 李國安 2005 學位論文 ; thesis 99 zh-TW
collection NDLTD
language zh-TW
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description 碩士 === 輔仁大學 === 化學系 === 94 === 1-Bromo-2-phenylcyclopropene (55) was synthesized by treating 1,1,2- tribromo-2-phenylcyclopropane 52 with 1 eq. methyllithium. Cyclopropene (55) underwent [2+2] dimerization to give 1,2-dibromo-4,5-diphenyl- tricycle[3.1.0.02,4]hexane (57). When 57 was heated at toluene refluxing temperature, 1,2-dibromo4,5-diphenyl-1,4-cyclohexadiene (58) and 1,2- dibromo-4,5-diphenylbenzene (59) were obtained. Compound 58 could be oxidated to yield 59. Both 1-phenylcyclopropene and 55 can proceed [2+2] dimerization, therefore we could use the same character to get the crossed [2+2] cycloaddition adduct 1-bromo-2-hydrogen-4,5-diphenyltricyclo[3.1.0.02,4]- hexane 62. This is the first confirmed crossed [2+2] cycloaddition of cyclopropenes. When the adduct 62 was heated at toluene refluxing temperature for 5 hours, 1-bromo-4,5-diphenyl-1,4-cyclohexadiene (63) and 1-bromo-4,5-diphenylbenzene (64) were received. Compound 63 could be oxidated to yield 64.
author2 LEE GON-ANN
author_facet LEE GON-ANN
JIANG SHI-FEN
江詩芬
author JIANG SHI-FEN
江詩芬
spellingShingle JIANG SHI-FEN
江詩芬
〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
author_sort JIANG SHI-FEN
title 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
title_short 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
title_full 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
title_fullStr 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
title_full_unstemmed 〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes〔2+2〕Cycloadditions of Cyclopropenes
title_sort 〔2+2〕cycloadditions of cyclopropenes〔2+2〕cycloadditions of cyclopropenes〔2+2〕cycloadditions of cyclopropenes
publishDate 2005
url http://ndltd.ncl.edu.tw/handle/28893733061734407100
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