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

Download
  1. (PDF, 339 KB)
  2. Get@NRC: Toward a Reactant Library in Template-Directed Solid-State Organic Synthesis: Reactivity Involving a Monofunctional Reactant Based on a Stilbazole (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1021/ie010775w
AuthorSearch for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleIndustrial & Engineering Chemistry Research
ISSN0888-5885
Volume41
Issue18
Pages44944497; # of pages: 4
AbstractCocrystallization 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.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier10413844
NPARC number12327554
Export citationExport as RIS
Report a correctionReport a correction
Record identifier7d4022d5-ab21-46c9-9100-6d876c20c38a
Record created2009-09-10
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)