Toward a Reactant Library in Template-Directed Solid-State Organic Synthesis: Reactivity Involving a Monofunctional Reactant Based on a Stilbazole

Autor:	Giannis S. Papaefstathiou, Leonard R. MacGillivray, John A. Ripmeester, Jennifer L. Reid
Rok vydání:	2002
Předmět:	Hydrogen bond Chemistry Stereochemistry General Chemical Engineering General Chemistry Chemical synthesis Industrial and Manufacturing Engineering Cyclobutane chemistry.chemical_compound Molecular solid Covalent bond Yield (chemistry) Polymer chemistry Reactivity (chemistry) Organic synthesis
Zdroj:	Industrial & Engineering Chemistry Research. 41:4494-4497
ISSN:	1520-5045 0888-5885
DOI:	10.1021/ie010775w
Popis:	Cocrystallization of 4-chlorostilbazole (4-Cl-sbz) with either resorcinol (res) or 4-ethylresorcinol (4-Et-res) yields three-component molecular assemblies, (res)‚2(4-Cl-sbz) and (4-Et-res)‚2(4-Clsbz), held together by two O-H‚‚‚N hydrogen bonds. The olefins of each assembly conform to the distance criterion of Schmidt for [2+2] photoreaction. In the former, the olefins lie antiparallel, whereas in the latter, the olefins lie parallel. Both solids are photoactive, leading to the regiocontrolled solid-state synthesis of rctt-1,2-bis(4-pyridyl)-3,4-bis(4-chlorophenyl)cyclobutane (4-Cl-dpcb) in near or quantitative yield. The photoactivity of (res)‚2(4-Cl-sbz) is attributed to the reactant undergoing a pedal-like change in conformation prior to cyclobutane formation. The ability to change the diol to achieve olefin alignment is expected to provide additional synthetic flexibility to this template approach. The realization that covalent bonds can form in molecular solids 1 suggests a possibility that the solid
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::63aa76902d222f7d8f9a467ac9eba061 https://doi.org/10.1021/ie010775w Zobrazit plný text záznamu