Thermally Stable Aromatic Structures from Acyclic Precursors. 1. Para-Polyphenylene Model Compounds from 3-Dimethylaminohex-5-EN-1-YNES.
Abstract
Condensation of N,N-dimethyl-(3phenylprop-2-ynyl) amines with cinnamyl bromides of various structure afford cinnamyldimethyl-(3-phenylprop-2-vinyl) ammonium bromides in high yield. Without isolation, the ammonium salts can undergo both (3,2) and (1,2) base catalyzed Stevens rearrangements to the corresponding 3-dimethylamino-1,4-diphenylhex-5-en-1-ynes. Subsequent heating of the rearranged products closes the (3,2) linkages preferentially forming the all para-polyphenyls which are isolated easily from the reaction mixtures.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jul 01, 1987
- Accession Number
- ADA185300
Entities
People
- Bruce A. Reinhardt
- Marilyn R. Unroe
Organizations
- Wright Laboratory