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Polar reactions of acyclic conjugated bisallenes.

ABSTRACT: The chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br(2) and I(2) addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.

SUBMITTER: Stamm R

PROVIDER: S-EPMC3566852 | biostudies-other | 2013

REPOSITORIES: biostudies-other

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Polar reactions of acyclic conjugated bisallenes.

Stamm Reiner R Hopf Henning H

Beilstein journal of organic chemistry 20130108

The chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br(2) and I(2) addition), and ...[more]

PMID: 23400309

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