Halogenoborane mediated allene cyclooligomerizationElectronic supplementary information (ESI) available: Additional experimental details, further spectral and crystallographic data. CCDC 1862533-1862535 and 1881527. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc04790a
The halogenoboranes XB(C 6 F 5 ) 2 (X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane ( 1 ) and the related halogenoborylated cyclotetramerization products 3a and 3b . Alkyl-substituted allenes were catalytically cyclotrimerized metal-free by XB(C 6 F 5...
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| Main Authors | , , , , |
|---|---|
| Format | Journal Article |
| Language | English |
| Published |
20.02.2019
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| Online Access | Get full text |
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| Abstract | The halogenoboranes XB(C
6
F
5
)
2
(X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane (
1
) and the related halogenoborylated cyclotetramerization products
3a
and
3b
. Alkyl-substituted allenes were catalytically cyclotrimerized metal-free by XB(C
6
F
5
)
2
(X: Cl, Br) to give
cis
,
trans
-2,4,6-trialkyl-1,3,5-trimethylenecyclohexanes under mild conditions.
Allene reacts with the strongly electrophilic halogenoboranes XB(C
6
F
5
)
2
(X: Cl or Br) by forming a mixture of 1,3,5-trimethylenecyclohexane and the stoichiometric halogeno-borated tetramerization products. |
|---|---|
| AbstractList | The halogenoboranes XB(C
6
F
5
)
2
(X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane (
1
) and the related halogenoborylated cyclotetramerization products
3a
and
3b
. Alkyl-substituted allenes were catalytically cyclotrimerized metal-free by XB(C
6
F
5
)
2
(X: Cl, Br) to give
cis
,
trans
-2,4,6-trialkyl-1,3,5-trimethylenecyclohexanes under mild conditions.
Allene reacts with the strongly electrophilic halogenoboranes XB(C
6
F
5
)
2
(X: Cl or Br) by forming a mixture of 1,3,5-trimethylenecyclohexane and the stoichiometric halogeno-borated tetramerization products. |
| Author | Kehr, Gerald Tao, Xin Daniliuc, Constantin G Erker, Gerhard Wölke, Christian |
| AuthorAffiliation | Westfälische Wilhelms-Universität Münster Organisch-Chemisches Institut |
| AuthorAffiliation_xml | – name: Organisch-Chemisches Institut – name: Westfälische Wilhelms-Universität Münster |
| Author_xml | – sequence: 1 givenname: Xin surname: Tao fullname: Tao, Xin – sequence: 2 givenname: Christian surname: Wölke fullname: Wölke, Christian – sequence: 3 givenname: Constantin G surname: Daniliuc fullname: Daniliuc, Constantin G – sequence: 4 givenname: Gerald surname: Kehr fullname: Kehr, Gerald – sequence: 5 givenname: Gerhard surname: Erker fullname: Erker, Gerhard |
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| Notes | For ESI and crystallographic data in CIF or other electronic format see DOI 1862533-1862535 10.1039/c8sc04790a and 1881527 Electronic supplementary information (ESI) available: Additional experimental details, further spectral and crystallographic data. CCDC |
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| References_xml | – issn: 2007 issue: vol. 44 publication-title: Cumulenes and Allenes, Science of Synthesis doi: Krause – issn: 1984 publication-title: Organoboron Compounds in Organic Synthesis doi: Mikhailov Bubnov – issn: 2004 publication-title: Modern Allene Chemistry doi: Krause Hashmi |
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| Snippet | The halogenoboranes XB(C
6
F
5
)
2
(X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane (
1
) and the related... |
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| Title | Halogenoborane mediated allene cyclooligomerizationElectronic supplementary information (ESI) available: Additional experimental details, further spectral and crystallographic data. CCDC 1862533-1862535 and 1881527. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc04790a |
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