A new route for the preparation of enriched iso-polylactide from rac-lactide via a Lewis acid catalyzed ring-opening of an epoxide
Tetraphenylporphyrin aluminum(iii) salts, TPPAlX, where X = Me, OEt, OiPr, OCHMeCH Cl, and Cl, and bis(triphenylphosphine)imminium chloride, PPN Cl (1 : 1) react with rac-lactide, rac-LA, in neat propylene oxide, PO, to yield chains of enriched isotactic polylactide, PLA, with end groups of PO-Cl an...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2017-05, Vol.46 (18), p.5938-5945 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Anker, Mathew Balasanthiran, Choumini Balasanthiran, Vagulejan Chisholm, Malcolm H Jayaraj, Savithra Mathieu, Kaleb Piromjitpong, Parichat Praban, Siriwan Raya, Balaram Simonsick, William J |
| description | Tetraphenylporphyrin aluminum(iii) salts, TPPAlX, where X = Me, OEt, OiPr, OCHMeCH
Cl, and Cl, and bis(triphenylphosphine)imminium chloride, PPN
Cl
(1 : 1) react with rac-lactide, rac-LA, in neat propylene oxide, PO, to yield chains of enriched isotactic polylactide, PLA, with end groups of PO-Cl and with time these yield cyclic polymers (PO)
(PLA) where n = 2 or 3 and even higher. There is no reaction between TPPAlOR (R = Et or
Pr), PPN
Cl
, and rac-LA in neat THF at 25 °C even though TPPAlOR (R = Et or
Pr) and PPN
Cl
in neat PO yields polypropylene oxide with a terminal OR group, H(PO)
OR. Taken together, Al(iii) acts as a Lewis acid in the ring-opening of PO, in which PPN
Cl
is present and the incipient ClCH
CHMeO
initiates the ROP of LA to yield anion chains of [(PLA)-OCHMeCH
Cl]
, and then the ring-opening of PO yields cycles, (PO)
(PLA), with the liberation of Cl
. The polymer was isolated by the addition of MeOH/HCl and end group analysis by mass spectrometry. |
| doi_str_mv | 10.1039/c6dt03198f |
| format | Article |
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Cl, and Cl, and bis(triphenylphosphine)imminium chloride, PPN
Cl
(1 : 1) react with rac-lactide, rac-LA, in neat propylene oxide, PO, to yield chains of enriched isotactic polylactide, PLA, with end groups of PO-Cl and with time these yield cyclic polymers (PO)
(PLA) where n = 2 or 3 and even higher. There is no reaction between TPPAlOR (R = Et or
Pr), PPN
Cl
, and rac-LA in neat THF at 25 °C even though TPPAlOR (R = Et or
Pr) and PPN
Cl
in neat PO yields polypropylene oxide with a terminal OR group, H(PO)
OR. Taken together, Al(iii) acts as a Lewis acid in the ring-opening of PO, in which PPN
Cl
is present and the incipient ClCH
CHMeO
initiates the ROP of LA to yield anion chains of [(PLA)-OCHMeCH
Cl]
, and then the ring-opening of PO yields cycles, (PO)
(PLA), with the liberation of Cl
. The polymer was isolated by the addition of MeOH/HCl and end group analysis by mass spectrometry.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c6dt03198f</identifier><identifier>PMID: 28418053</identifier><language>eng</language><publisher>England</publisher><subject>Anions ; Chlorides ; Enrichment ; Lewis acid ; Mass spectrometry ; Polylactides ; Polypropylene oxides ; Terminals</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2017-05, Vol.46 (18), p.5938-5945</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c320t-e7e02ab9e75292e7109b034f410ca2e84c8661d369d9bd1d1ab2aba7437878673</citedby><cites>FETCH-LOGICAL-c320t-e7e02ab9e75292e7109b034f410ca2e84c8661d369d9bd1d1ab2aba7437878673</cites><orcidid>0000-0003-0450-7370 ; 0000-0003-3950-6925 ; 0000-0002-4472-6239</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28418053$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Anker, Mathew</creatorcontrib><creatorcontrib>Balasanthiran, Choumini</creatorcontrib><creatorcontrib>Balasanthiran, Vagulejan</creatorcontrib><creatorcontrib>Chisholm, Malcolm H</creatorcontrib><creatorcontrib>Jayaraj, Savithra</creatorcontrib><creatorcontrib>Mathieu, Kaleb</creatorcontrib><creatorcontrib>Piromjitpong, Parichat</creatorcontrib><creatorcontrib>Praban, Siriwan</creatorcontrib><creatorcontrib>Raya, Balaram</creatorcontrib><creatorcontrib>Simonsick, William J</creatorcontrib><title>A new route for the preparation of enriched iso-polylactide from rac-lactide via a Lewis acid catalyzed ring-opening of an epoxide</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Tetraphenylporphyrin aluminum(iii) salts, TPPAlX, where X = Me, OEt, OiPr, OCHMeCH
Cl, and Cl, and bis(triphenylphosphine)imminium chloride, PPN
Cl
(1 : 1) react with rac-lactide, rac-LA, in neat propylene oxide, PO, to yield chains of enriched isotactic polylactide, PLA, with end groups of PO-Cl and with time these yield cyclic polymers (PO)
(PLA) where n = 2 or 3 and even higher. There is no reaction between TPPAlOR (R = Et or
Pr), PPN
Cl
, and rac-LA in neat THF at 25 °C even though TPPAlOR (R = Et or
Pr) and PPN
Cl
in neat PO yields polypropylene oxide with a terminal OR group, H(PO)
OR. Taken together, Al(iii) acts as a Lewis acid in the ring-opening of PO, in which PPN
Cl
is present and the incipient ClCH
CHMeO
initiates the ROP of LA to yield anion chains of [(PLA)-OCHMeCH
Cl]
, and then the ring-opening of PO yields cycles, (PO)
(PLA), with the liberation of Cl
. The polymer was isolated by the addition of MeOH/HCl and end group analysis by mass spectrometry.</description><subject>Anions</subject><subject>Chlorides</subject><subject>Enrichment</subject><subject>Lewis acid</subject><subject>Mass spectrometry</subject><subject>Polylactides</subject><subject>Polypropylene oxides</subject><subject>Terminals</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkblOxDAURS0EYm_4AOQSIQW8TWyXaFilkWigjl7sFzDKxMHOAEPJl5Nha6nu09O5p7mEHHB2wpm0p670A5PcmmaNbHOldWGFVOt_tyi3yE7OT4wJwSZik2wJo7hhE7lNPs5oh680xcWAtImJDo9I-4Q9JBhC7GhsKHYpuEf0NORY9LFdtuCG4Ec-xTlN4Irfx0sACnSGryFTcMFTBwO0y_exm0L3UMQeuzFXUugo9vFtbO2RjQbajPs_uUvuLy_uptfF7PbqZno2K5wUbChQIxNQW9QTYQVqzmzNpGoUZw4EGuVMWXIvS-tt7bnnUI84aCW10abUcpccfXv7FJ8XmIdqHrLDtoUO4yJX3DLFrVVM_I8aY6WR2q6sx9-oSzHnhE3VpzCHtKw4q1bzVNPy_O5rnssRPvzxLuo5-j_0dw_5CTopivY</recordid><startdate>20170509</startdate><enddate>20170509</enddate><creator>Anker, Mathew</creator><creator>Balasanthiran, Choumini</creator><creator>Balasanthiran, Vagulejan</creator><creator>Chisholm, Malcolm H</creator><creator>Jayaraj, Savithra</creator><creator>Mathieu, Kaleb</creator><creator>Piromjitpong, Parichat</creator><creator>Praban, Siriwan</creator><creator>Raya, Balaram</creator><creator>Simonsick, William J</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-0450-7370</orcidid><orcidid>https://orcid.org/0000-0003-3950-6925</orcidid><orcidid>https://orcid.org/0000-0002-4472-6239</orcidid></search><sort><creationdate>20170509</creationdate><title>A new route for the preparation of enriched iso-polylactide from rac-lactide via a Lewis acid catalyzed ring-opening of an epoxide</title><author>Anker, Mathew ; Balasanthiran, Choumini ; Balasanthiran, Vagulejan ; Chisholm, Malcolm H ; Jayaraj, Savithra ; Mathieu, Kaleb ; Piromjitpong, Parichat ; Praban, Siriwan ; Raya, Balaram ; Simonsick, William J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-e7e02ab9e75292e7109b034f410ca2e84c8661d369d9bd1d1ab2aba7437878673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Anions</topic><topic>Chlorides</topic><topic>Enrichment</topic><topic>Lewis acid</topic><topic>Mass spectrometry</topic><topic>Polylactides</topic><topic>Polypropylene oxides</topic><topic>Terminals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Anker, Mathew</creatorcontrib><creatorcontrib>Balasanthiran, Choumini</creatorcontrib><creatorcontrib>Balasanthiran, Vagulejan</creatorcontrib><creatorcontrib>Chisholm, Malcolm H</creatorcontrib><creatorcontrib>Jayaraj, Savithra</creatorcontrib><creatorcontrib>Mathieu, Kaleb</creatorcontrib><creatorcontrib>Piromjitpong, Parichat</creatorcontrib><creatorcontrib>Praban, Siriwan</creatorcontrib><creatorcontrib>Raya, Balaram</creatorcontrib><creatorcontrib>Simonsick, William J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Anker, Mathew</au><au>Balasanthiran, Choumini</au><au>Balasanthiran, Vagulejan</au><au>Chisholm, Malcolm H</au><au>Jayaraj, Savithra</au><au>Mathieu, Kaleb</au><au>Piromjitpong, Parichat</au><au>Praban, Siriwan</au><au>Raya, Balaram</au><au>Simonsick, William J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new route for the preparation of enriched iso-polylactide from rac-lactide via a Lewis acid catalyzed ring-opening of an epoxide</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2017-05-09</date><risdate>2017</risdate><volume>46</volume><issue>18</issue><spage>5938</spage><epage>5945</epage><pages>5938-5945</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Tetraphenylporphyrin aluminum(iii) salts, TPPAlX, where X = Me, OEt, OiPr, OCHMeCH
Cl, and Cl, and bis(triphenylphosphine)imminium chloride, PPN
Cl
(1 : 1) react with rac-lactide, rac-LA, in neat propylene oxide, PO, to yield chains of enriched isotactic polylactide, PLA, with end groups of PO-Cl and with time these yield cyclic polymers (PO)
(PLA) where n = 2 or 3 and even higher. There is no reaction between TPPAlOR (R = Et or
Pr), PPN
Cl
, and rac-LA in neat THF at 25 °C even though TPPAlOR (R = Et or
Pr) and PPN
Cl
in neat PO yields polypropylene oxide with a terminal OR group, H(PO)
OR. Taken together, Al(iii) acts as a Lewis acid in the ring-opening of PO, in which PPN
Cl
is present and the incipient ClCH
CHMeO
initiates the ROP of LA to yield anion chains of [(PLA)-OCHMeCH
Cl]
, and then the ring-opening of PO yields cycles, (PO)
(PLA), with the liberation of Cl
. The polymer was isolated by the addition of MeOH/HCl and end group analysis by mass spectrometry.</abstract><cop>England</cop><pmid>28418053</pmid><doi>10.1039/c6dt03198f</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-0450-7370</orcidid><orcidid>https://orcid.org/0000-0003-3950-6925</orcidid><orcidid>https://orcid.org/0000-0002-4472-6239</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2017-05, Vol.46 (18), p.5938-5945 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anions Chlorides Enrichment Lewis acid Mass spectrometry Polylactides Polypropylene oxides Terminals |
| title | A new route for the preparation of enriched iso-polylactide from rac-lactide via a Lewis acid catalyzed ring-opening of an epoxide |
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