Dimerization of Cubene. 1-Iodoadamantane as a Probe for Radical Intermediates

Fluoride ion induced elimination from 1-bromo- and 1-iodo-2-(trimethyisilyl)cubanes is shown to produce cubene (1) in excellent yield and at high enough concentration for its dimerization to propellane 16. This highly strained compound is unstable; the ultimate reaction pro ducts are characterized a...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 117; no. 29; pp. 7652 - 7656
Main Authors Lukin, Kirill, Eaton, Philip E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.1995
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
1,2-DEHYDROCUBANE
ACIDS
CHEMISTRY
ABINITIO CALCULATIONS
GENERATION
ENERGIES
FLUORIDE
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Summary:Fluoride ion induced elimination from 1-bromo- and 1-iodo-2-(trimethyisilyl)cubanes is shown to produce cubene (1) in excellent yield and at high enough concentration for its dimerization to propellane 16. This highly strained compound is unstable; the ultimate reaction pro ducts are characterized as the isomeric bis(tricyclo[4.2.0.0(2,5)]-octa-3,7-diene-3,8-diyl)s 11a,b. These are believed to form via a set of radical ring openings of 16. 1-Iodoadamantane is introduced as an iodine atom donor useful for probing the intermediacy of radicals in the chemistry of highly reactive, strained ring systems such as 16.
Bibliography:ark:/67375/TPS-MQK2GXZF-N
istex:2D2AE4B9C397C80504D74242B89FB50DECB8CC44
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00134a009