נגישות
menu      
Advanced Search
Syntax
Search...
Volcani treasures
About
Terms of use
Manage
Community:
אסיף מאגר המחקר החקלאי
Powered by ClearMash Solutions Ltd -
Solid-state photooligomerization of an extended chiral bifunctional monomer, (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate
Year:
1980
Authors :
Rejtö, Miriam
;
.
Volume :
102
Co-Authors:
Bernstein, J., Chemistry Department, Ben-Gurion University of the Negev, Beersheva, Israel
Green, B.S., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Rejtö, M., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Facilitators :
From page:
323
To page:
328
(
Total pages:
6
)
Abstract:
Irradiation of crystalline (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate (1) induces intermolecular cyclobutane formation leading to chiral oligomers of increasing length. The dimer, trimer, tetramer, and pentamer have been isolated and characterized. The intramolecular distance between the olefinic residues within the molecules of 1 is larger than in any previous examples of solid-state photodimerization or oligomerization and, in spite of the large, bulky tetraoxa-cis-decalin group separating the reaction centers, the cinnamate groups of the monomer are properly aligned for intermolecular photocycloaddition. Crystals of 1 are monoclinic, a = 15.218 (6) Å, b = 13.217 (7) Å, c = 5.882 (3) Å, β = 76.95 (3)°; the space group is P21, with two molecules in the cell. The structure has been solved by direct methods and refined to an R factor of 0.043 on 2270 nonzero reflections. The crystal structure analysis establishes the correct molecular structure of the sugar alcohol derivative, previously in doubt, and elucidates the molecular packing which is responsible for the observed products. The chemical consequences of solid-state irradiation of compound 12, a monothiophene analogue of 1, have been considered; 12, however, shows an unexpected reluctance to crystallize in the same structure as 1. © 1980 American Chemical Society.
Note:
Related Files :
Show More
Related Content
More details
DOI :
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
21121
Last updated date:
02/03/2022 17:27
Creation date:
16/04/2018 23:41
Scientific Publication
Solid-state photooligomerization of an extended chiral bifunctional monomer, (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate
102
Bernstein, J., Chemistry Department, Ben-Gurion University of the Negev, Beersheva, Israel
Green, B.S., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Rejtö, M., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Solid-state photooligomerization of an extended chiral bifunctional monomer, (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate
Irradiation of crystalline (+)-2,4:3,5-di-O-methylene-D-mannitol 1,6-di-trans-cinnamate (1) induces intermolecular cyclobutane formation leading to chiral oligomers of increasing length. The dimer, trimer, tetramer, and pentamer have been isolated and characterized. The intramolecular distance between the olefinic residues within the molecules of 1 is larger than in any previous examples of solid-state photodimerization or oligomerization and, in spite of the large, bulky tetraoxa-cis-decalin group separating the reaction centers, the cinnamate groups of the monomer are properly aligned for intermolecular photocycloaddition. Crystals of 1 are monoclinic, a = 15.218 (6) Å, b = 13.217 (7) Å, c = 5.882 (3) Å, β = 76.95 (3)°; the space group is P21, with two molecules in the cell. The structure has been solved by direct methods and refined to an R factor of 0.043 on 2270 nonzero reflections. The crystal structure analysis establishes the correct molecular structure of the sugar alcohol derivative, previously in doubt, and elucidates the molecular packing which is responsible for the observed products. The chemical consequences of solid-state irradiation of compound 12, a monothiophene analogue of 1, have been considered; 12, however, shows an unexpected reluctance to crystallize in the same structure as 1. © 1980 American Chemical Society.
Scientific Publication
You may also be interested in