Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism

Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism

Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoa...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 1997-09, Vol.62 (18), p.6152-6159
Hauptverfasser: Wong, Jim-Wah, Natalie, Kenneth J, Nwokogu, Godson C, Pisipati, Jyothi S, Flaherty, Patrick T, Greenwood, Thomas D, Wolfe, James F
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 6159
container_issue 18
container_start_page 6152
container_title Journal of organic chemistry
container_volume 62
creator Wong, Jim-Wah
Natalie, Kenneth J
Nwokogu, Godson C
Pisipati, Jyothi S
Flaherty, Patrick T
Greenwood, Thomas D
Wolfe, James F
description Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the SRN1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).
doi_str_mv 10.1021/jo962353f
format Article
fullrecord <record><control><sourceid>istex_acs_j</sourceid><recordid>TN_cdi_istex_primary_ark_67375_TPS_4C6LZ5B1_Q</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_TPS_4C6LZ5B1_Q</sourcerecordid><originalsourceid>FETCH-LOGICAL-a136t-b81fc63e97f038090aac3885fed9b942b9f4023f23a359a7528edf8b3ebce7bc3</originalsourceid><addsrcrecordid>eNpNkE1LAzEYhIMoWKsH_0EuHlfzsdndHHVRK9T60erBS0jShE3dbUqSRfvv3VIR5_Iy8MzwMgCcY3SJEcFXK88LQhm1B2CEGUFZwVF-CEYIEZJRUtBjcBLjCg1ijI1ArH23kckp17q0hd7Cdxmc7yOsZVBy7fwaznrdGr9pXGsi_HKpgROTTPAy-G6I6n_AYOa9ismlPu2iagtTY-D8dYbho9HNUBi7U3BkZRvN2e8dg7e720U9yaZP9w_19TSTmBYpUxW2uqCGlxbRCnEkpaZVxaxZcsVzorjNEaGWUEkZlyUjlVnaSlGjtCmVpmOQ7XtdTOZbbILrZNgKGT5FUdKSicXzXOR1Mf1gN1i8DPzFnpc6ipXvw3r4TmAkdsuKv2XpD9Q1bUI</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism</title><source>American Chemical Society Journals</source><creator>Wong, Jim-Wah ; Natalie, Kenneth J ; Nwokogu, Godson C ; Pisipati, Jyothi S ; Flaherty, Patrick T ; Greenwood, Thomas D ; Wolfe, James F</creator><creatorcontrib>Wong, Jim-Wah ; Natalie, Kenneth J ; Nwokogu, Godson C ; Pisipati, Jyothi S ; Flaherty, Patrick T ; Greenwood, Thomas D ; Wolfe, James F</creatorcontrib><description>Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the SRN1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo962353f</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 1997-09, Vol.62 (18), p.6152-6159</ispartof><rights>Copyright © 1997 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo962353f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo962353f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Wong, Jim-Wah</creatorcontrib><creatorcontrib>Natalie, Kenneth J</creatorcontrib><creatorcontrib>Nwokogu, Godson C</creatorcontrib><creatorcontrib>Pisipati, Jyothi S</creatorcontrib><creatorcontrib>Flaherty, Patrick T</creatorcontrib><creatorcontrib>Greenwood, Thomas D</creatorcontrib><creatorcontrib>Wolfe, James F</creatorcontrib><title>Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the SRN1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><recordid>eNpNkE1LAzEYhIMoWKsH_0EuHlfzsdndHHVRK9T60erBS0jShE3dbUqSRfvv3VIR5_Iy8MzwMgCcY3SJEcFXK88LQhm1B2CEGUFZwVF-CEYIEZJRUtBjcBLjCg1ijI1ArH23kckp17q0hd7Cdxmc7yOsZVBy7fwaznrdGr9pXGsi_HKpgROTTPAy-G6I6n_AYOa9ismlPu2iagtTY-D8dYbho9HNUBi7U3BkZRvN2e8dg7e720U9yaZP9w_19TSTmBYpUxW2uqCGlxbRCnEkpaZVxaxZcsVzorjNEaGWUEkZlyUjlVnaSlGjtCmVpmOQ7XtdTOZbbILrZNgKGT5FUdKSicXzXOR1Mf1gN1i8DPzFnpc6ipXvw3r4TmAkdsuKv2XpD9Q1bUI</recordid><startdate>19970905</startdate><enddate>19970905</enddate><creator>Wong, Jim-Wah</creator><creator>Natalie, Kenneth J</creator><creator>Nwokogu, Godson C</creator><creator>Pisipati, Jyothi S</creator><creator>Flaherty, Patrick T</creator><creator>Greenwood, Thomas D</creator><creator>Wolfe, James F</creator><general>American Chemical Society</general><scope>BSCLL</scope></search><sort><creationdate>19970905</creationdate><title>Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism</title><author>Wong, Jim-Wah ; Natalie, Kenneth J ; Nwokogu, Godson C ; Pisipati, Jyothi S ; Flaherty, Patrick T ; Greenwood, Thomas D ; Wolfe, James F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a136t-b81fc63e97f038090aac3885fed9b942b9f4023f23a359a7528edf8b3ebce7bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wong, Jim-Wah</creatorcontrib><creatorcontrib>Natalie, Kenneth J</creatorcontrib><creatorcontrib>Nwokogu, Godson C</creatorcontrib><creatorcontrib>Pisipati, Jyothi S</creatorcontrib><creatorcontrib>Flaherty, Patrick T</creatorcontrib><creatorcontrib>Greenwood, Thomas D</creatorcontrib><creatorcontrib>Wolfe, James F</creatorcontrib><collection>Istex</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wong, Jim-Wah</au><au>Natalie, Kenneth J</au><au>Nwokogu, Godson C</au><au>Pisipati, Jyothi S</au><au>Flaherty, Patrick T</au><au>Greenwood, Thomas D</au><au>Wolfe, James F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1997-09-05</date><risdate>1997</risdate><volume>62</volume><issue>18</issue><spage>6152</spage><epage>6159</epage><pages>6152-6159</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the SRN1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).</abstract><pub>American Chemical Society</pub><doi>10.1021/jo962353f</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 1997-09, Vol.62 (18), p.6152-6159
issn 0022-3263
1520-6904
language eng
recordid cdi_istex_primary_ark_67375_TPS_4C6LZ5B1_Q
source American Chemical Society Journals
title Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T17%3A14%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Compatibility%20of%20Various%20Carbanion%20Nucleophiles%20with%20Heteroaromatic%20Nucleophilic%20Substitution%20by%20the%20SRN1%20Mechanism&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Wong,%20Jim-Wah&rft.date=1997-09-05&rft.volume=62&rft.issue=18&rft.spage=6152&rft.epage=6159&rft.pages=6152-6159&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo962353f&rft_dat=%3Cistex_acs_j%3Eark_67375_TPS_4C6LZ5B1_Q%3C/istex_acs_j%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true