Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand
The complex [(dpp-bian) − Ga(σ-allyl)Cl] ( 1 ), which was prepared by the oxidative addition of two equivalents of allyl chloride to digallane [(dpp-bian) 2− Ga—Ga(dpp-bian) 2− ], reacts with one equivalent of sodium in tetrahydrofuran (THF) at 40 °C to afford the complex [(dpp-bian) 2− (THF)Ga] 2 (...
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| Veröffentlicht in: | Russian chemical bulletin 2023-11, Vol.72 (11), p.2667-2676 |
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| creator | Dodonov, V. A. Kushnerova, O. A. Baranov, E. V. Fedushkin, I. L. |
| description | The complex [(dpp-bian)
−
Ga(σ-allyl)Cl] (
1
), which was prepared by the oxidative addition of two equivalents of allyl chloride to digallane [(dpp-bian)
2−
Ga—Ga(dpp-bian)
2−
], reacts with one equivalent of sodium in tetrahydrofuran (THF) at 40 °C to afford the complex [(dpp-bian)
2−
(THF)Ga]
2
(µ
2
-1,3-C
3
H
6
) (
2
), in which two gallium atoms are connected by the bridging propane-1,3-diyl moiety. Under more harsh conditions (80 °C), this reaction gives asymmetric anionic digallane [(dpp-bian)Ga—Ga(dpp-bian)(σ-C
9
H
13
)]
−
(
3
) with the [Na(Et
2
O)
3
(THF)]
+
cation as the counterion. The σ-H
13
moiety in digallane
3
resulted from the cyclotrimerization of three allyl radicals. Compounds
2
and
3
were characterized by IR spectroscopy, multinuclear NMR spectroscopy, and elemental analysis. Their molecular structures were determined by single-crystal X-ray diffraction. Compounds
2
and
3
are unique because they contain the previously unknown metal fragments M—CH
2
CH
2
CH
2
—M and σ-C
9
H
13
—M, respectively. It is suggested that these complexes are produced
via
cascade β-elimination, carbo- and hydrogallation reactions. |
| doi_str_mv | 10.1007/s11172-023-4071-z |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2907790996</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2907790996</sourcerecordid><originalsourceid>FETCH-LOGICAL-c316t-2472f153b7678dcec935b5686340fda54accd0aa8f59fc654e87a8c200f608c33</originalsourceid><addsrcrecordid>eNp1kF1LwzAUhosoOKc_wLuA19GTtPnopQy_YOCNuw5ZmnQdbVOTVrf9ejMmeOXV-eB9zoEny24J3BMA8RAJIYJioDkuQBB8OMtmhIkcl0SQ89QD55hRyS6zqxi3AECllLOsXvV2N1gz2gqNQffR-dDpsfF9RN4h3SPdtvsW1cFPA2rSiOq0aaYOGd8Nrd2h72bcoHFjUbCV32FtxubLomoY8LpJfNvUuq-uswun22hvfus8Wz0_fSxe8fL95W3xuMQmJ3zEtBDUEZavBReyMtaUOVszLnlegKs0K7QxFWgtHSud4aywUmhpKIDjIE2ez7O7090h-M_JxlFt_RT69FLREoQooSx5SpFTygQfY7BODaHpdNgrAuroU518quRTHX2qQ2LoiYkp29c2_F3-H_oBBfh5zg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2907790996</pqid></control><display><type>article</type><title>Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand</title><source>SpringerLink Journals - AutoHoldings</source><creator>Dodonov, V. A. ; Kushnerova, O. A. ; Baranov, E. V. ; Fedushkin, I. L.</creator><creatorcontrib>Dodonov, V. A. ; Kushnerova, O. A. ; Baranov, E. V. ; Fedushkin, I. L.</creatorcontrib><description>The complex [(dpp-bian)
−
Ga(σ-allyl)Cl] (
1
), which was prepared by the oxidative addition of two equivalents of allyl chloride to digallane [(dpp-bian)
2−
Ga—Ga(dpp-bian)
2−
], reacts with one equivalent of sodium in tetrahydrofuran (THF) at 40 °C to afford the complex [(dpp-bian)
2−
(THF)Ga]
2
(µ
2
-1,3-C
3
H
6
) (
2
), in which two gallium atoms are connected by the bridging propane-1,3-diyl moiety. Under more harsh conditions (80 °C), this reaction gives asymmetric anionic digallane [(dpp-bian)Ga—Ga(dpp-bian)(σ-C
9
H
13
)]
−
(
3
) with the [Na(Et
2
O)
3
(THF)]
+
cation as the counterion. The σ-H
13
moiety in digallane
3
resulted from the cyclotrimerization of three allyl radicals. Compounds
2
and
3
were characterized by IR spectroscopy, multinuclear NMR spectroscopy, and elemental analysis. Their molecular structures were determined by single-crystal X-ray diffraction. Compounds
2
and
3
are unique because they contain the previously unknown metal fragments M—CH
2
CH
2
CH
2
—M and σ-C
9
H
13
—M, respectively. It is suggested that these complexes are produced
via
cascade β-elimination, carbo- and hydrogallation reactions.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-023-4071-z</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Allyl chloride ; Chemical analysis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Equivalence ; Full Articles ; Gallium ; Infrared spectroscopy ; Inorganic Chemistry ; Molecular structure ; NMR spectroscopy ; Organic Chemistry ; Single crystals ; Sodium ; Tetrahydrofuran</subject><ispartof>Russian chemical bulletin, 2023-11, Vol.72 (11), p.2667-2676</ispartof><rights>Springer Science+Business Media LLC 2023</rights><rights>Springer Science+Business Media LLC 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-2472f153b7678dcec935b5686340fda54accd0aa8f59fc654e87a8c200f608c33</citedby><cites>FETCH-LOGICAL-c316t-2472f153b7678dcec935b5686340fda54accd0aa8f59fc654e87a8c200f608c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-023-4071-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-023-4071-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Dodonov, V. A.</creatorcontrib><creatorcontrib>Kushnerova, O. A.</creatorcontrib><creatorcontrib>Baranov, E. V.</creatorcontrib><creatorcontrib>Fedushkin, I. L.</creatorcontrib><title>Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>The complex [(dpp-bian)
−
Ga(σ-allyl)Cl] (
1
), which was prepared by the oxidative addition of two equivalents of allyl chloride to digallane [(dpp-bian)
2−
Ga—Ga(dpp-bian)
2−
], reacts with one equivalent of sodium in tetrahydrofuran (THF) at 40 °C to afford the complex [(dpp-bian)
2−
(THF)Ga]
2
(µ
2
-1,3-C
3
H
6
) (
2
), in which two gallium atoms are connected by the bridging propane-1,3-diyl moiety. Under more harsh conditions (80 °C), this reaction gives asymmetric anionic digallane [(dpp-bian)Ga—Ga(dpp-bian)(σ-C
9
H
13
)]
−
(
3
) with the [Na(Et
2
O)
3
(THF)]
+
cation as the counterion. The σ-H
13
moiety in digallane
3
resulted from the cyclotrimerization of three allyl radicals. Compounds
2
and
3
were characterized by IR spectroscopy, multinuclear NMR spectroscopy, and elemental analysis. Their molecular structures were determined by single-crystal X-ray diffraction. Compounds
2
and
3
are unique because they contain the previously unknown metal fragments M—CH
2
CH
2
CH
2
—M and σ-C
9
H
13
—M, respectively. It is suggested that these complexes are produced
via
cascade β-elimination, carbo- and hydrogallation reactions.</description><subject>Allyl chloride</subject><subject>Chemical analysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Equivalence</subject><subject>Full Articles</subject><subject>Gallium</subject><subject>Infrared spectroscopy</subject><subject>Inorganic Chemistry</subject><subject>Molecular structure</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Single crystals</subject><subject>Sodium</subject><subject>Tetrahydrofuran</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kF1LwzAUhosoOKc_wLuA19GTtPnopQy_YOCNuw5ZmnQdbVOTVrf9ejMmeOXV-eB9zoEny24J3BMA8RAJIYJioDkuQBB8OMtmhIkcl0SQ89QD55hRyS6zqxi3AECllLOsXvV2N1gz2gqNQffR-dDpsfF9RN4h3SPdtvsW1cFPA2rSiOq0aaYOGd8Nrd2h72bcoHFjUbCV32FtxubLomoY8LpJfNvUuq-uswun22hvfus8Wz0_fSxe8fL95W3xuMQmJ3zEtBDUEZavBReyMtaUOVszLnlegKs0K7QxFWgtHSud4aywUmhpKIDjIE2ez7O7090h-M_JxlFt_RT69FLREoQooSx5SpFTygQfY7BODaHpdNgrAuroU518quRTHX2qQ2LoiYkp29c2_F3-H_oBBfh5zg</recordid><startdate>20231101</startdate><enddate>20231101</enddate><creator>Dodonov, V. A.</creator><creator>Kushnerova, O. A.</creator><creator>Baranov, E. V.</creator><creator>Fedushkin, I. L.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231101</creationdate><title>Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand</title><author>Dodonov, V. A. ; Kushnerova, O. A. ; Baranov, E. V. ; Fedushkin, I. L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-2472f153b7678dcec935b5686340fda54accd0aa8f59fc654e87a8c200f608c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Allyl chloride</topic><topic>Chemical analysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Equivalence</topic><topic>Full Articles</topic><topic>Gallium</topic><topic>Infrared spectroscopy</topic><topic>Inorganic Chemistry</topic><topic>Molecular structure</topic><topic>NMR spectroscopy</topic><topic>Organic Chemistry</topic><topic>Single crystals</topic><topic>Sodium</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dodonov, V. A.</creatorcontrib><creatorcontrib>Kushnerova, O. A.</creatorcontrib><creatorcontrib>Baranov, E. V.</creatorcontrib><creatorcontrib>Fedushkin, I. L.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dodonov, V. A.</au><au>Kushnerova, O. A.</au><au>Baranov, E. V.</au><au>Fedushkin, I. L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2023-11-01</date><risdate>2023</risdate><volume>72</volume><issue>11</issue><spage>2667</spage><epage>2676</epage><pages>2667-2676</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>The complex [(dpp-bian)
−
Ga(σ-allyl)Cl] (
1
), which was prepared by the oxidative addition of two equivalents of allyl chloride to digallane [(dpp-bian)
2−
Ga—Ga(dpp-bian)
2−
], reacts with one equivalent of sodium in tetrahydrofuran (THF) at 40 °C to afford the complex [(dpp-bian)
2−
(THF)Ga]
2
(µ
2
-1,3-C
3
H
6
) (
2
), in which two gallium atoms are connected by the bridging propane-1,3-diyl moiety. Under more harsh conditions (80 °C), this reaction gives asymmetric anionic digallane [(dpp-bian)Ga—Ga(dpp-bian)(σ-C
9
H
13
)]
−
(
3
) with the [Na(Et
2
O)
3
(THF)]
+
cation as the counterion. The σ-H
13
moiety in digallane
3
resulted from the cyclotrimerization of three allyl radicals. Compounds
2
and
3
were characterized by IR spectroscopy, multinuclear NMR spectroscopy, and elemental analysis. Their molecular structures were determined by single-crystal X-ray diffraction. Compounds
2
and
3
are unique because they contain the previously unknown metal fragments M—CH
2
CH
2
CH
2
—M and σ-C
9
H
13
—M, respectively. It is suggested that these complexes are produced
via
cascade β-elimination, carbo- and hydrogallation reactions.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-023-4071-z</doi><tpages>10</tpages></addata></record> |
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| issn | 1066-5285 1573-9171 |
| language | eng |
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| source | SpringerLink Journals - AutoHoldings |
| subjects | Allyl chloride Chemical analysis Chemistry Chemistry and Materials Science Chemistry/Food Science Equivalence Full Articles Gallium Infrared spectroscopy Inorganic Chemistry Molecular structure NMR spectroscopy Organic Chemistry Single crystals Sodium Tetrahydrofuran |
| title | Unexpected transformations of an allyl group in a gallium complex with the redox-active dpp-bian ligand |
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