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- Title
Short Access to Belt Compounds with Spatially Close CC Bonds and Their Transannular Reactions.
- Authors
Camps, Pelayo; Gómez, Tània; Otermin, Ane; Font ‐ Bardia, Mercè; Estarellas, Carolina; Luque, Francisco Javier
- Abstract
Two domino Diels-Alder adducts were obtained from 3,7-bis(cyclopenta-2,4-dien-1-ylidene)- cis-bicyclo[3.3.0]octane and dimethyl acetylenedicarboxylate or N-methylmaleimide under microwave irradiation. From the first adduct, a C20H24 diene with C2 v symmetry was obtained by Zn/AcOH reduction, hydrolysis, oxidative decarboxylation, and selective hydrogenation. Photochemical [2+2] cycloaddition of this diene gave a thermally unstable cyclobutane derivative, which reverts to the diene. However, both the diene and the cyclobutane derivatives could be identified by X-ray diffraction analysis upon irradiation of the diene crystal. New six-membered rings are formed upon the transannular addition of bromine or iodine to the diene. The N-type selectivity of the addition was examined by theoretical calculations, which revealed the distinct susceptibility of the doubly bonded carbon atoms to the bromine attack.
- Subjects
CYCLOPENTADIENE; CARBON-carbon bonds; ANNULATION; DIELS-Alder reaction; CYCLOBUTANE; HYDROGENATION; ACETYLENE compounds; X-ray diffraction
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 40, p14036
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201502351