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Selenium halide-induced bridge formation in [2.2]paracyclophanes.

ABSTRACT: An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size.

SUBMITTER: Sarbu LG

PROVIDER: S-EPMC4222412 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Selenium halide-induced bridge formation in [2.2]paracyclophanes.

Sarbu Laura G LG Hopf Henning H Jones Peter G PG Birsa Lucian M LM

Beilstein journal of organic chemistry 20141031

An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size. ...[more]

PMID: 25383126

Similar Datasets

Building complex carbon skeletons with ethynyl[2.2]paracyclophanes.

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