Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage
Cyclization of allyl[3-(4-bromophenyl)prop-2-ynyl]ammonium bromides under basic catalysis conditions, unlike their propargyl analogs, occurs under heating of the reaction mixture at 90–92°C. Cyclization, which is the main reaction route, is accompanied by rearrangement-cleavage to form 1-allyl- p -b...
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| Veröffentlicht in: | Russian journal of organic chemistry 2019-08, Vol.55 (8), p.1124-1130 |
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| container_title | Russian journal of organic chemistry |
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| creator | Chukhajian, E. O. Ayrapetyan, L. V. Mkrtchyan, H. S. Chukhajian, El. O. Panosyan, H. A. |
| description | Cyclization of allyl[3-(4-bromophenyl)prop-2-ynyl]ammonium bromides under basic catalysis conditions, unlike their propargyl analogs, occurs under heating of the reaction mixture at 90–92°C. Cyclization, which is the main reaction route, is accompanied by rearrangement-cleavage to form 1-allyl-
p
-bromocinnamaldehyde. A favorable effect of the substituents on the nitrogen atom and the presence of the bromine atom in the
4
position of the aromatic ring on the cyclization and rearrangement-cleavage reactions is established. |
| doi_str_mv | 10.1134/S1070428019080104 |
| format | Article |
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p
-bromocinnamaldehyde. A favorable effect of the substituents on the nitrogen atom and the presence of the bromine atom in the
4
position of the aromatic ring on the cyclization and rearrangement-cleavage reactions is established.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428019080104</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Ammonium bromides ; Aromatic compounds ; Bromides ; Bromine ; Chemistry ; Chemistry and Materials Science ; Cleavage ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2019-08, Vol.55 (8), p.1124-1130</ispartof><rights>Pleiades Publishing, Ltd. 2019</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-1f2679c23e95639192f3472abcf503a0c85b42a7769286c865ead2381f03aa003</citedby><cites>FETCH-LOGICAL-c316t-1f2679c23e95639192f3472abcf503a0c85b42a7769286c865ead2381f03aa003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428019080104$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428019080104$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids></links><search><creatorcontrib>Chukhajian, E. O.</creatorcontrib><creatorcontrib>Ayrapetyan, L. V.</creatorcontrib><creatorcontrib>Mkrtchyan, H. S.</creatorcontrib><creatorcontrib>Chukhajian, El. O.</creatorcontrib><creatorcontrib>Panosyan, H. A.</creatorcontrib><title>Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>Cyclization of allyl[3-(4-bromophenyl)prop-2-ynyl]ammonium bromides under basic catalysis conditions, unlike their propargyl analogs, occurs under heating of the reaction mixture at 90–92°C. Cyclization, which is the main reaction route, is accompanied by rearrangement-cleavage to form 1-allyl-
p
-bromocinnamaldehyde. A favorable effect of the substituents on the nitrogen atom and the presence of the bromine atom in the
4
position of the aromatic ring on the cyclization and rearrangement-cleavage reactions is established.</description><subject>Ammonium bromides</subject><subject>Aromatic compounds</subject><subject>Bromides</subject><subject>Bromine</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cleavage</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxYMoWKsfwFvAq9FJJpvdPdbiPxA8tJ5ElnQ3aVO3m5p0hfrpTangQbzMDLzfmxkeIeccrjhHeT3hkIMUBfASUgF5QAZcQcEQSzxMc5LZTj8mJzEuAUByiQNST7bdZmGii9RbqthN8CvPUF9K1rjFtgl-Zrov_2rfXPSua3zrOtev6I5zjYlUdw2dLowLdPTRG99HNmrfdaIMHbdGf-q5OSVHVrfRnP30IXm5u52OH9jT8_3jePTEauRqw7gVKi9rgabMFJa8FBZlLvSsthmghrrIZlLoPFelKFRdqMzoRmDBbVI1AA7JxX7vOvj0S9xUS9-HLp2sBKZgUAkoEsX3VB18jMHYah3cSodtxaHaZVn9yTJ5xN4TE9vNTfjd_L_pG3rNdII</recordid><startdate>20190801</startdate><enddate>20190801</enddate><creator>Chukhajian, E. O.</creator><creator>Ayrapetyan, L. V.</creator><creator>Mkrtchyan, H. S.</creator><creator>Chukhajian, El. O.</creator><creator>Panosyan, H. A.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20190801</creationdate><title>Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage</title><author>Chukhajian, E. O. ; Ayrapetyan, L. V. ; Mkrtchyan, H. S. ; Chukhajian, El. O. ; Panosyan, H. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-1f2679c23e95639192f3472abcf503a0c85b42a7769286c865ead2381f03aa003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Ammonium bromides</topic><topic>Aromatic compounds</topic><topic>Bromides</topic><topic>Bromine</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cleavage</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chukhajian, E. O.</creatorcontrib><creatorcontrib>Ayrapetyan, L. V.</creatorcontrib><creatorcontrib>Mkrtchyan, H. S.</creatorcontrib><creatorcontrib>Chukhajian, El. O.</creatorcontrib><creatorcontrib>Panosyan, H. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chukhajian, E. O.</au><au>Ayrapetyan, L. V.</au><au>Mkrtchyan, H. S.</au><au>Chukhajian, El. O.</au><au>Panosyan, H. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2019-08-01</date><risdate>2019</risdate><volume>55</volume><issue>8</issue><spage>1124</spage><epage>1130</epage><pages>1124-1130</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>Cyclization of allyl[3-(4-bromophenyl)prop-2-ynyl]ammonium bromides under basic catalysis conditions, unlike their propargyl analogs, occurs under heating of the reaction mixture at 90–92°C. Cyclization, which is the main reaction route, is accompanied by rearrangement-cleavage to form 1-allyl-
p
-bromocinnamaldehyde. A favorable effect of the substituents on the nitrogen atom and the presence of the bromine atom in the
4
position of the aromatic ring on the cyclization and rearrangement-cleavage reactions is established.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428019080104</doi><tpages>7</tpages></addata></record> |
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| subjects | Ammonium bromides Aromatic compounds Bromides Bromine Chemistry Chemistry and Materials Science Cleavage Organic Chemistry |
| title | Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage |
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