Unexpected halogen exchange with halogenated solvents in the iron(III) promoted oxa-alkyne and aza-alkyne Prins cyclizations

Irradiation of 1-fluoro-, 1-chloro-, and 1-bromoadamantanes in halogenated solvents leads to free radical halogenation of the adamantane skeleton without exchange of the 1-halo atom. Reactions in tetrachloromethane yield products substituted at both the secondary carbons (i.e., bridge carbons) and at tertiary bridgehead carbons. Bridgehead substituted bromo-products greatly predominate when bromotrichloromethane is used as a solvent. Using this difference in the type of products formed from CCl4 and BrCCl3 a variety of mixed-halo substituted adamantanes were prepared from 1-monohaloadamantanes. Irradiation of 1-iodoadamantane in either solvent proceeds initially only with halogen exchange rather than halogenation of the ring system.

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Radical polymerization in halogenated solvents—II. Methyl methacrylate polymerization initiated by benzoyl peroxide

European Polymer Journal ◽

10.1016/0014-3057(69)90120-7 ◽

1969 ◽

Vol 5 (1) ◽

pp. 231-237 ◽

Cited By ~ 14

Author(s):

G.M. Burnett ◽

G.G. Cameron ◽

Brenda M. Parker

Keyword(s):

Methyl Methacrylate ◽

Benzoyl Peroxide ◽

Radical Polymerization ◽

Methyl Methacrylate Polymerization ◽

Halogenated Solvents

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ChemInform Abstract: EVIDENCE FOR AN INDIRECT HALOGEN EXCHANGE IN THE REACTION OF TRANS-2,3-DIBROMO-2,3-DIHYDROBENZOFURAN WITH CHLORIDE IONS

Chemischer Informationsdienst ◽

10.1002/chin.197818166 ◽

1978 ◽

Vol 9 (18) ◽

Author(s):

E. BACIOCCHI ◽

S. CLEMENTI ◽

R. RUZZICONI ◽

G. V. SEBASTIANI

Keyword(s):

Chloride Ions ◽

Halogen Exchange

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Reversible Chain Transfer Catalyzed Polymerization with Alkyl Iodides Generated from Alkyl Bromides by in Situ Halogen Exchange

Chinese Journal of Polymer Science ◽

10.1007/s10118-021-2611-2 ◽

2021 ◽

Author(s):

Dan-Ni Gao ◽

Yu-Lai Zhao ◽

Jing-Yu Cai ◽

Lin-Xi Hou ◽

Long-Qiang Xiao

Keyword(s):

Chain Transfer ◽

Alkyl Bromides ◽

Halogen Exchange ◽

Reversible Chain Transfer ◽

Alkyl Iodides ◽

Catalyzed Polymerization

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Pentaalkyl-Derivate des 2 ,3 - Dihiydro-1,3-diborols/Pentaalkyl Derivatives of the 2,3-Dihydro-1,3-diborole

Zeitschrift für Naturforschung B ◽

10.1515/znb-1990-0105 ◽

1990 ◽

Vol 45 (1) ◽

pp. 15-18 ◽

Cited By ~ 19

Author(s):

G . Knörzer ◽

W. Siebert

Keyword(s):

Redox Reactions ◽

Halogen Exchange ◽

Derivatives Of

AbstractDouble hydroboration of acetylene, propyne-1 and t-butylacetylene with HBCl2 · OEt2/BCl3 leads to the 1,1-bis(dichloroboryl)alkanes 2d, e, f, in which halogen exchange is achieved by BI3 to give 3d, e, f. Redox reactions between butyne-2, hexyne-3 and 3 result in the formation of compounds 4, which are alkylated with AlMe3 and AlEt3 to give the pentaalkyl derivatives 1d, e, f. Reactions of 1 with [(C5H5)Co(C2H4)2] an [(C5H5)N iCO]2 lead to the complexes 5 and 6.

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