TY - JOUR
T1 - Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols
T2 - Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies
AU - Ericson, Devin P.
AU - Zurfluh-Cunningham, Zachary P.
AU - Groeneman, Ryan H.
AU - Elacqua, Elizabeth
AU - Reinheimer, Eric W.
AU - Noll, Bruce C.
AU - MacGillivray, Leonard R.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/10/21
Y1 - 2015/10/21
N2 - Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.
AB - Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.
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U2 - 10.1021/acs.cgd.5b00939
DO - 10.1021/acs.cgd.5b00939
M3 - Article
AN - SCOPUS:84948653994
VL - 15
SP - 5744
EP - 5748
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 12
ER -