Synthesis, Characterization, and Structure of Some 1,4-Disubstituted Cyclopenta[d][1,2]oxazines

Autor:	Eric M. Collins, Darrin L. Smith, Edwin D. Stevens, Nathan C. Tice, Bangbo Yan, Chad A. Snyder
Rok vydání:	2017
Předmět:	chemistry.chemical_classification 010405 organic chemistry Organic Chemistry Stacking Infrared spectroscopy Oxazines 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Monomer Hydroxylamine chemistry Polymer chemistry Thiophene Pyrrole
Zdroj:	Journal of Heterocyclic Chemistry. 54:3235-3240
ISSN:	0022-152X
DOI:	10.1002/jhet.2941
Popis:	Oxazine-based chemistry offers an alternative to thiophene and pyrrole semiconductors and has been largely unexplored for electronics applications. Discrete monomers or oxazine polymers could serve as an efficient hole carrier for novel devices. A series of 1,4-disubstituted cyclopenta[d][1,2]oxazines (R = tolyl, p-nitrophenyl, t-buytl, furyl, and 5-methylthienyl) were isolated via ring closure with hydroxylamine from a 1,2-acylcyclopentadiene precursor. The target oxazines were characterized by NMR and IR spectroscopy and direct analysis in real time (DART) MS. Single-crystal x-ray structure determination confirmed the identity of the tolyl oxazine, which shows a face-to-face stacking pattern of the heterocyclic rings.
Databáze:	OpenAIRE
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