Dehalogenation of 1,3-diiodotricyclo[3.3.0.0(3,7)]octane: generation of 1,3-dehydrotricyclo[3.3.0.0(3,7)]octane, a 2,5-methano-bridged [2.2.1]propellane

Ayats, C; Camps, P; Fernández, JA; Vázquez, S

HERO ID

1071123

Reference Type

Journal Article

Year

2007

Language

English

PMID

17091516

HERO ID 1071123
In Press No
Year 2007
Title Dehalogenation of 1,3-diiodotricyclo[3.3.0.0(3,7)]octane: generation of 1,3-dehydrotricyclo[3.3.0.0(3,7)]octane, a 2,5-methano-bridged [2.2.1]propellane
Authors Ayats, C; Camps, P; Fernández, JA; Vázquez, S
Journal Chemistry: A European Journal
Volume 13
Issue 5
Page Numbers 1522-1532
Abstract Compounds isolated from the reaction of (+/-)-1,3-diiodotricyclo[3.3.0.0(3,7)]octane with molten sodium or tBuLi suggest the intermediate formation of (+/-)-1,3-dehydrotricyclo[3.3.0.0(3,7)]octane. Worthy of note is the formation of stereoisomeric bi(5-methylenebicyclo[2.2.1]hept-2-ylidene) derivatives, probably by coupling of two units of (+/-)-1,3-dehydrotricyclo[3.3.0.0(3,7)]octane of the same or different absolute configuration followed by fragmentation, processes that have been studied by theoretical calculations.
Doi 10.1002/chem.200600859
Pmid 17091516
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Language Text English
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