Hydrogallierungsreaktionen mit den Monoalkinen H 5 C 6 ‐C≡C‐SiMe 3 und H 5 C 6 ‐C≡C‐CMe 3 – cis / trans ‐Isomerie und Substituentenaustausch
Hydrogallation Reactions Involving the Monoalkynes H 5 C 6 ‐C≡C‐SiMe 3 and H 5 C 6 ‐C≡C‐CMe 3 – cis / trans Isomerisation and Substituent Exchange Phenyl‐trimethylsilylethyne, H 5 C 6 ‐C≡C‐SiMe 3 , reacted with different dialkylgallium hydrides, R 2 Ga‐H (R = Me, Et, n Pr, i Pr, t Bu), by the additi...
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| Veröffentlicht in: | Zeitschrift für anorganische und allgemeine Chemie (1950) 2008-12, Vol.634 (15), p.2889-2896 |
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| container_title | Zeitschrift für anorganische und allgemeine Chemie (1950) |
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| creator | Uhl, Werner Claesener, Michael Haddadpour, Sima Jasper, Beate Tiesmeyer, Ines Zemke, Sarina |
| description | Hydrogallation Reactions Involving the Monoalkynes H
5
C
6
‐C≡C‐SiMe
3
and H
5
C
6
‐C≡C‐CMe
3
–
cis
/
trans
Isomerisation and Substituent Exchange
Phenyl‐trimethylsilylethyne, H
5
C
6
‐C≡C‐SiMe
3
, reacted with different dialkylgallium hydrides, R
2
Ga‐H (R = Me, Et,
n
Pr,
i
Pr,
t
Bu), by the addition of one Ga‐H bond to its C≡C triple bond (hydrogallation). The gallium atoms attacked selectively those carbon atoms, which were also attached to trimethylsilyl groups. The
cis
arrangement of Ga and H across the resulting C=C double bonds resulted only for the sterically most shielded di(
tert
‐butyl)gallium derivative, while in all other cases spontaneous
cis
/
trans
rearrangement occurred with the quantitative formation of the
trans
addition products. The diethyl compound Et
2
Ga‐C(SiMe
3
)=C(H)‐C
6
H
5
(
2
) gave by substituent exchange the secondary products EtGa[C(SiMe
3
)=C(H)‐C
6
H
5
]
2
(
7
,
Z
,
Z
) and Ga[C(SiMe
3
)=C(H)‐C
6
H
5
]
3
(
8
). Interestingly, compound
8
has two alkenyl groups with a
Z
configuration, while the third C=C double bond has the
cis
arrangement of Ga and H (
E
configuration). The reversibility of the
cis
/
trans
isomerisation of hydrogallation products was observed for the first time.
tert
‐Butyl‐phenylethyne gave the simple addition product, R
2
Ga(C
6
H
5
)=C(H)‐CMe
3
(
9
), only with di(
n
‐propyl)gallium hydride. |
| doi_str_mv | 10.1002/zaac.200800322 |
| format | Article |
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5
C
6
‐C≡C‐SiMe
3
and H
5
C
6
‐C≡C‐CMe
3
–
cis
/
trans
Isomerisation and Substituent Exchange
Phenyl‐trimethylsilylethyne, H
5
C
6
‐C≡C‐SiMe
3
, reacted with different dialkylgallium hydrides, R
2
Ga‐H (R = Me, Et,
n
Pr,
i
Pr,
t
Bu), by the addition of one Ga‐H bond to its C≡C triple bond (hydrogallation). The gallium atoms attacked selectively those carbon atoms, which were also attached to trimethylsilyl groups. The
cis
arrangement of Ga and H across the resulting C=C double bonds resulted only for the sterically most shielded di(
tert
‐butyl)gallium derivative, while in all other cases spontaneous
cis
/
trans
rearrangement occurred with the quantitative formation of the
trans
addition products. The diethyl compound Et
2
Ga‐C(SiMe
3
)=C(H)‐C
6
H
5
(
2
) gave by substituent exchange the secondary products EtGa[C(SiMe
3
)=C(H)‐C
6
H
5
]
2
(
7
,
Z
,
Z
) and Ga[C(SiMe
3
)=C(H)‐C
6
H
5
]
3
(
8
). Interestingly, compound
8
has two alkenyl groups with a
Z
configuration, while the third C=C double bond has the
cis
arrangement of Ga and H (
E
configuration). The reversibility of the
cis
/
trans
isomerisation of hydrogallation products was observed for the first time.
tert
‐Butyl‐phenylethyne gave the simple addition product, R
2
Ga(C
6
H
5
)=C(H)‐CMe
3
(
9
), only with di(
n
‐propyl)gallium hydride.</description><identifier>ISSN: 0044-2313</identifier><identifier>EISSN: 1521-3749</identifier><identifier>DOI: 10.1002/zaac.200800322</identifier><language>eng</language><ispartof>Zeitschrift für anorganische und allgemeine Chemie (1950), 2008-12, Vol.634 (15), p.2889-2896</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c842-cae96cd40cec3edb6d66f20f3accc13673cfaecb1bb3217272e537885c3442403</citedby><cites>FETCH-LOGICAL-c842-cae96cd40cec3edb6d66f20f3accc13673cfaecb1bb3217272e537885c3442403</cites></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>Uhl, Werner</creatorcontrib><creatorcontrib>Claesener, Michael</creatorcontrib><creatorcontrib>Haddadpour, Sima</creatorcontrib><creatorcontrib>Jasper, Beate</creatorcontrib><creatorcontrib>Tiesmeyer, Ines</creatorcontrib><creatorcontrib>Zemke, Sarina</creatorcontrib><title>Hydrogallierungsreaktionen mit den Monoalkinen H 5 C 6 ‐C≡C‐SiMe 3 und H 5 C 6 ‐C≡C‐CMe 3 – cis / trans ‐Isomerie und Substituentenaustausch</title><title>Zeitschrift für anorganische und allgemeine Chemie (1950)</title><description>Hydrogallation Reactions Involving the Monoalkynes H
5
C
6
‐C≡C‐SiMe
3
and H
5
C
6
‐C≡C‐CMe
3
–
cis
/
trans
Isomerisation and Substituent Exchange
Phenyl‐trimethylsilylethyne, H
5
C
6
‐C≡C‐SiMe
3
, reacted with different dialkylgallium hydrides, R
2
Ga‐H (R = Me, Et,
n
Pr,
i
Pr,
t
Bu), by the addition of one Ga‐H bond to its C≡C triple bond (hydrogallation). The gallium atoms attacked selectively those carbon atoms, which were also attached to trimethylsilyl groups. The
cis
arrangement of Ga and H across the resulting C=C double bonds resulted only for the sterically most shielded di(
tert
‐butyl)gallium derivative, while in all other cases spontaneous
cis
/
trans
rearrangement occurred with the quantitative formation of the
trans
addition products. The diethyl compound Et
2
Ga‐C(SiMe
3
)=C(H)‐C
6
H
5
(
2
) gave by substituent exchange the secondary products EtGa[C(SiMe
3
)=C(H)‐C
6
H
5
]
2
(
7
,
Z
,
Z
) and Ga[C(SiMe
3
)=C(H)‐C
6
H
5
]
3
(
8
). Interestingly, compound
8
has two alkenyl groups with a
Z
configuration, while the third C=C double bond has the
cis
arrangement of Ga and H (
E
configuration). The reversibility of the
cis
/
trans
isomerisation of hydrogallation products was observed for the first time.
tert
‐Butyl‐phenylethyne gave the simple addition product, R
2
Ga(C
6
H
5
)=C(H)‐CMe
3
(
9
), only with di(
n
‐propyl)gallium hydride.</description><issn>0044-2313</issn><issn>1521-3749</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNptkLtOw0AQRVcIJEKgpd4fcDL78CMlsoBESkSR9NZ6vA5LnDXatYtQpaVDSkvDr-VLsAOiohgdae6dKQ4htwxGDICP35TCEQdIAATnZ2TAQs4CEcvJORkASBlwwcQlufL-BQAYhOGAfE53havXqqqMdq1de6fVpjG11ZZuTUOLjova1qramH43pSFNaUSP-4_0-P6VdlyahaaCtrb4L01P4XF_oGg8HdPGKev7wszXW-2MPh0u29w3pmm1bbRVrW-6wedrclGqyuubXw7J6uF-lU6D-dPjLL2bB5hIHqDSkwgLCahR6CKPiigqOZRCISITUSywVBpzlueCs5jHXIciTpIQhZRcghiS0c9bdLXvBJTZqzNb5XYZg6xXm_Vqsz-14htSy3PF</recordid><startdate>200812</startdate><enddate>200812</enddate><creator>Uhl, Werner</creator><creator>Claesener, Michael</creator><creator>Haddadpour, Sima</creator><creator>Jasper, Beate</creator><creator>Tiesmeyer, Ines</creator><creator>Zemke, Sarina</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200812</creationdate><title>Hydrogallierungsreaktionen mit den Monoalkinen H 5 C 6 ‐C≡C‐SiMe 3 und H 5 C 6 ‐C≡C‐CMe 3 – cis / trans ‐Isomerie und Substituentenaustausch</title><author>Uhl, Werner ; Claesener, Michael ; Haddadpour, Sima ; Jasper, Beate ; Tiesmeyer, Ines ; Zemke, Sarina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c842-cae96cd40cec3edb6d66f20f3accc13673cfaecb1bb3217272e537885c3442403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uhl, Werner</creatorcontrib><creatorcontrib>Claesener, Michael</creatorcontrib><creatorcontrib>Haddadpour, Sima</creatorcontrib><creatorcontrib>Jasper, Beate</creatorcontrib><creatorcontrib>Tiesmeyer, Ines</creatorcontrib><creatorcontrib>Zemke, Sarina</creatorcontrib><collection>CrossRef</collection><jtitle>Zeitschrift für anorganische und allgemeine Chemie (1950)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uhl, Werner</au><au>Claesener, Michael</au><au>Haddadpour, Sima</au><au>Jasper, Beate</au><au>Tiesmeyer, Ines</au><au>Zemke, Sarina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogallierungsreaktionen mit den Monoalkinen H 5 C 6 ‐C≡C‐SiMe 3 und H 5 C 6 ‐C≡C‐CMe 3 – cis / trans ‐Isomerie und Substituentenaustausch</atitle><jtitle>Zeitschrift für anorganische und allgemeine Chemie (1950)</jtitle><date>2008-12</date><risdate>2008</risdate><volume>634</volume><issue>15</issue><spage>2889</spage><epage>2896</epage><pages>2889-2896</pages><issn>0044-2313</issn><eissn>1521-3749</eissn><abstract>Hydrogallation Reactions Involving the Monoalkynes H
5
C
6
‐C≡C‐SiMe
3
and H
5
C
6
‐C≡C‐CMe
3
–
cis
/
trans
Isomerisation and Substituent Exchange
Phenyl‐trimethylsilylethyne, H
5
C
6
‐C≡C‐SiMe
3
, reacted with different dialkylgallium hydrides, R
2
Ga‐H (R = Me, Et,
n
Pr,
i
Pr,
t
Bu), by the addition of one Ga‐H bond to its C≡C triple bond (hydrogallation). The gallium atoms attacked selectively those carbon atoms, which were also attached to trimethylsilyl groups. The
cis
arrangement of Ga and H across the resulting C=C double bonds resulted only for the sterically most shielded di(
tert
‐butyl)gallium derivative, while in all other cases spontaneous
cis
/
trans
rearrangement occurred with the quantitative formation of the
trans
addition products. The diethyl compound Et
2
Ga‐C(SiMe
3
)=C(H)‐C
6
H
5
(
2
) gave by substituent exchange the secondary products EtGa[C(SiMe
3
)=C(H)‐C
6
H
5
]
2
(
7
,
Z
,
Z
) and Ga[C(SiMe
3
)=C(H)‐C
6
H
5
]
3
(
8
). Interestingly, compound
8
has two alkenyl groups with a
Z
configuration, while the third C=C double bond has the
cis
arrangement of Ga and H (
E
configuration). The reversibility of the
cis
/
trans
isomerisation of hydrogallation products was observed for the first time.
tert
‐Butyl‐phenylethyne gave the simple addition product, R
2
Ga(C
6
H
5
)=C(H)‐CMe
3
(
9
), only with di(
n
‐propyl)gallium hydride.</abstract><doi>10.1002/zaac.200800322</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0044-2313 |
| ispartof | Zeitschrift für anorganische und allgemeine Chemie (1950), 2008-12, Vol.634 (15), p.2889-2896 |
| issn | 0044-2313 1521-3749 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_zaac_200800322 |
| source | Wiley Journals |
| title | Hydrogallierungsreaktionen mit den Monoalkinen H 5 C 6 ‐C≡C‐SiMe 3 und H 5 C 6 ‐C≡C‐CMe 3 – cis / trans ‐Isomerie und Substituentenaustausch |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T04%3A29%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Hydrogallierungsreaktionen%20mit%20den%20Monoalkinen%20H%205%20C%206%20%E2%80%90C%E2%89%A1C%E2%80%90SiMe%203%20und%20H%205%20C%206%20%E2%80%90C%E2%89%A1C%E2%80%90CMe%203%20%E2%80%93%20cis%20/%20trans%20%E2%80%90Isomerie%20und%20Substituentenaustausch&rft.jtitle=Zeitschrift%20f%C3%BCr%20anorganische%20und%20allgemeine%20Chemie%20(1950)&rft.au=Uhl,%20Werner&rft.date=2008-12&rft.volume=634&rft.issue=15&rft.spage=2889&rft.epage=2896&rft.pages=2889-2896&rft.issn=0044-2313&rft.eissn=1521-3749&rft_id=info:doi/10.1002/zaac.200800322&rft_dat=%3Ccrossref%3E10_1002_zaac_200800322%3C/crossref%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 |