Nucleophilic Displacement Reactions of Hexachlorocyclopentadiene II

Alternative Title

Reactions with secondary amines

Author

Earl T. McBee
James O. Stoffer, Missouri University of Science and TechnologyFollow
H. P. Braendlin

Abstract

In a continued study of reactions undergone by hexachlorocyclopentadiene with nucleophiles, the halide was treated with secondary aliphatic amines to give 5,5-diamino-1,2,3,4-tetrachlorocyclopentadienes. Allyl alcohol reacted with 5,5-dimorpholinyl-1,2,3,4-tetrachlorocyclopentadiene to give 5,7-methyleneoxy-7-morpholinyl-1,2,3,4-tetrachlorobicyclo[2.2.1]-hept-2-ene, an intramolecular Diels-Alder adduct, which on hydrolysis produced exo-5-hydroxymethyl-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2-en-7-one.

Recommended Citation

E. T. McBee et al., "Nucleophilic Displacement Reactions of Hexachlorocyclopentadiene II," Journal of the American Chemical Society, American Chemical Society (ACS), Jan 1962.

The definitive version is available at https://doi.org/10.1021/ja00882a033

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0002-7863

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1962 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Jan 1962