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Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation

Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation
Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation
Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a,b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a,b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl- 1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.
0022-3263
9140-9143
Terrasson, Vincent
28abd553-801c-415a-a09f-ff32adb54107
Planas, Jose G.
7754474e-807f-40db-b9e4-f2b00c10c388
Prim, Damien
0f74e921-8f1c-4916-830f-36f0cc5f85f9
Vinas, Clara
2a648a88-dae7-44dd-88e8-6d7220689d8a
Teixidor, Francesc
d24b81b5-5d82-42ca-bd30-fd9c73d0ee68
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Terrasson, Vincent
28abd553-801c-415a-a09f-ff32adb54107
Planas, Jose G.
7754474e-807f-40db-b9e4-f2b00c10c388
Prim, Damien
0f74e921-8f1c-4916-830f-36f0cc5f85f9
Vinas, Clara
2a648a88-dae7-44dd-88e8-6d7220689d8a
Teixidor, Francesc
d24b81b5-5d82-42ca-bd30-fd9c73d0ee68
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Terrasson, Vincent, Planas, Jose G., Prim, Damien, Vinas, Clara, Teixidor, Francesc, Light, Mark Edward and Hursthouse, Michael B. (2008) Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation. Journal of Organic Chemistry, 73 (22), 9140-9143. (doi:10.1021/jo801672f).

Record type: Article

Abstract

Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a,b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a,b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl- 1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.

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Published date: 21 November 2008

Identifiers

Local EPrints ID: 67663
URI: http://eprints.soton.ac.uk/id/eprint/67663
ISSN: 0022-3263
PURE UUID: cea7fbfc-e281-46c1-b84e-cce84d9a267c
ORCID for Mark Edward Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 02 Sep 2009
Last modified: 26 Nov 2019 01:55

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Contributors

Author: Vincent Terrasson
Author: Jose G. Planas
Author: Damien Prim
Author: Clara Vinas
Author: Francesc Teixidor

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