Loading…

Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions

The molybdenum benzylidynes [ArCMo­(OC­(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)­C6H4 (2b), p-(CF3)­C6H4 (2c), p-(NO2)­C6H4 (2d), or 4-(NO2)-3-(CF3)­C6H3 (2e), and [p-(NO2)­C6H4CMo­(OC­(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylami...

Full description

Saved in:
Bibliographic Details
Published in:Organometallics 2020-10, Vol.39 (19), p.3453-3457
Main Authors: Chuprun, Sergey, Acosta, Carlos M, Mathivathanan, Logesh, Bukhryakov, Konstantin V
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3
cites cdi_FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3
container_end_page 3457
container_issue 19
container_start_page 3453
container_title Organometallics
container_volume 39
creator Chuprun, Sergey
Acosta, Carlos M
Mathivathanan, Logesh
Bukhryakov, Konstantin V
description The molybdenum benzylidynes [ArCMo­(OC­(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)­C6H4 (2b), p-(CF3)­C6H4 (2c), p-(NO2)­C6H4 (2d), or 4-(NO2)-3-(CF3)­C6H3 (2e), and [p-(NO2)­C6H4CMo­(OC­(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.
doi_str_mv 10.1021/acs.organomet.0c00491
format article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_organomet_0c00491</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>b701672458</sourcerecordid><originalsourceid>FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3</originalsourceid><addsrcrecordid>eNqFkMtKxDAYhYMoWEcfQegLtP65tLE7tXiDGQZE1yVJ_2iHNhmSDlif3g4zuHV1FofvcPgIuaaQU2D0RpmY-_CpnB9wzMEAiIqekIQWDLISBD0lCTBZZpJzfk4uYtwAQCk5S8jdyveTbtHthvQB3c_Ud-3kMK39sO3xG2NqfUjXPdrOpSsc1fiFsYvpGyozdt7FS3JmVR_x6pgL8vH0-F6_ZMv182t9v8wUq4oxa1tbtZRJXVgjtGICtWVaoGIaqYVWMCMB8LbiaARlVilJpUJgQnNpEfmCFIddE3yMAW2zDd2gwtRQaPYamllD86ehOWqYOXrg9vXG74KbX_7D_AKz8mfY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Chuprun, Sergey ; Acosta, Carlos M ; Mathivathanan, Logesh ; Bukhryakov, Konstantin V</creator><creatorcontrib>Chuprun, Sergey ; Acosta, Carlos M ; Mathivathanan, Logesh ; Bukhryakov, Konstantin V</creatorcontrib><description>The molybdenum benzylidynes [ArCMo­(OC­(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)­C6H4 (2b), p-(CF3)­C6H4 (2c), p-(NO2)­C6H4 (2d), or 4-(NO2)-3-(CF3)­C6H3 (2e), and [p-(NO2)­C6H4CMo­(OC­(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/acs.organomet.0c00491</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2020-10, Vol.39 (19), p.3453-3457</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3</citedby><cites>FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3</cites><orcidid>0000-0002-8425-9671</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Chuprun, Sergey</creatorcontrib><creatorcontrib>Acosta, Carlos M</creatorcontrib><creatorcontrib>Mathivathanan, Logesh</creatorcontrib><creatorcontrib>Bukhryakov, Konstantin V</creatorcontrib><title>Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>The molybdenum benzylidynes [ArCMo­(OC­(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)­C6H4 (2b), p-(CF3)­C6H4 (2c), p-(NO2)­C6H4 (2d), or 4-(NO2)-3-(CF3)­C6H3 (2e), and [p-(NO2)­C6H4CMo­(OC­(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkMtKxDAYhYMoWEcfQegLtP65tLE7tXiDGQZE1yVJ_2iHNhmSDlif3g4zuHV1FofvcPgIuaaQU2D0RpmY-_CpnB9wzMEAiIqekIQWDLISBD0lCTBZZpJzfk4uYtwAQCk5S8jdyveTbtHthvQB3c_Ud-3kMK39sO3xG2NqfUjXPdrOpSsc1fiFsYvpGyozdt7FS3JmVR_x6pgL8vH0-F6_ZMv182t9v8wUq4oxa1tbtZRJXVgjtGICtWVaoGIaqYVWMCMB8LbiaARlVilJpUJgQnNpEfmCFIddE3yMAW2zDd2gwtRQaPYamllD86ehOWqYOXrg9vXG74KbX_7D_AKz8mfY</recordid><startdate>20201012</startdate><enddate>20201012</enddate><creator>Chuprun, Sergey</creator><creator>Acosta, Carlos M</creator><creator>Mathivathanan, Logesh</creator><creator>Bukhryakov, Konstantin V</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-8425-9671</orcidid></search><sort><creationdate>20201012</creationdate><title>Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions</title><author>Chuprun, Sergey ; Acosta, Carlos M ; Mathivathanan, Logesh ; Bukhryakov, Konstantin V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chuprun, Sergey</creatorcontrib><creatorcontrib>Acosta, Carlos M</creatorcontrib><creatorcontrib>Mathivathanan, Logesh</creatorcontrib><creatorcontrib>Bukhryakov, Konstantin V</creatorcontrib><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chuprun, Sergey</au><au>Acosta, Carlos M</au><au>Mathivathanan, Logesh</au><au>Bukhryakov, Konstantin V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2020-10-12</date><risdate>2020</risdate><volume>39</volume><issue>19</issue><spage>3453</spage><epage>3457</epage><pages>3453-3457</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>The molybdenum benzylidynes [ArCMo­(OC­(CF3)2CH3)3(1,2-dimethoxyethane)], where Ar = Ph (2a), p-(OCH3)­C6H4 (2b), p-(CF3)­C6H4 (2c), p-(NO2)­C6H4 (2d), or 4-(NO2)-3-(CF3)­C6H3 (2e), and [p-(NO2)­C6H4CMo­(OC­(CF3)2CH3)3] (2f) catalyze the ring-closing metathesis (RCM) reaction of diallyl N-tosylamide (3) to produce 1-tosyl-2,5-dihydro-1H-pyrrole (4) and ethylene. The scope of RCM catalytic activity of 2e, cross-metathesis of 1-hexene, and ring-opening metathesis polymerization of cyclooctene were explored. The X-ray crystal structure of 2e was determined. Variable-temperature 1H NMR spectra revealed the formation of intermediates during the reaction of 3 with 2f and the reforming of 2f after completion of the reaction. The use of 13C-labeled Mo benzylidyne did not show transfer of the carbon atom next to Mo to any of the products.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.organomet.0c00491</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8425-9671</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2020-10, Vol.39 (19), p.3453-3457
issn 0276-7333
1520-6041
language eng
recordid cdi_crossref_primary_10_1021_acs_organomet_0c00491
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Molybdenum Benzylidyne Complexes for Olefin Metathesis Reactions
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T17%3A42%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Molybdenum%20Benzylidyne%20Complexes%20for%20Olefin%20Metathesis%20Reactions&rft.jtitle=Organometallics&rft.au=Chuprun,%20Sergey&rft.date=2020-10-12&rft.volume=39&rft.issue=19&rft.spage=3453&rft.epage=3457&rft.pages=3453-3457&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/acs.organomet.0c00491&rft_dat=%3Cacs_cross%3Eb701672458%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a295t-ddf9d127b5fc4ba24ebf2b4ea2be1f0d42c700e893ec412faa717ae024b37fee3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true