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

Leonard R Macgillivray; Jennifer L Reid; John A Ripmeester; Giannis S Papaefstathiou

doi:10.1021/ie010775w

Back

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

Journal article

Open access

Peer reviewed

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

Leonard R Macgillivray, Jennifer L Reid, John A Ripmeester and Giannis S Papaefstathiou

Industrial & engineering chemistry research, Vol.41(18), pp.4494-4497

09/04/2002

DOI: 10.1021/ie010775w

Files and links (1)

url

https://doi.org/10.1021/ie010775wView

Published (Version of record) Open Access

Abstract

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-Cl-sbz), 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.

Details

Title: Subtitle: Toward a Reactant Library in Template-Directed Solid-State Organic Synthesis: Reactivity Involving a Monofunctional Reactant Based on a Stilbazole
Creators: Leonard R Macgillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa, 52242-1294, and Steacie Institute forMolecular Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
Jennifer L Reid - Department of Chemistry, University of Iowa, Iowa City, Iowa, 52242-1294, and Steacie Institute forMolecular Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
John A Ripmeester - Department of Chemistry, University of Iowa, Iowa City, Iowa, 52242-1294, and Steacie Institute forMolecular Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
Giannis S Papaefstathiou - Department of Chemistry, University of Iowa, Iowa City, Iowa, 52242-1294, and Steacie Institute forMolecular Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
Resource Type: Journal article
Publication Details: Industrial & engineering chemistry research, Vol.41(18), pp.4494-4497
DOI: 10.1021/ie010775w
ISSN: 0888-5885
eISSN: 1520-5045
Publisher: American Chemical Society
Language: English
Date published: 09/04/2002
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216690902771

Metrics

11 Record Views

34 Times Cited - Web of Science