Cycloaddition reactions of oxaquadricyclane, oxanorbornadiene, and relatedcompounds with cyclooctyne

Authors
Matsumoto, K Taketsuna, H Ikemi, Y Kakehi, A Uchida, T Otani, S
Citation
K. Matsumoto et al., Cycloaddition reactions of oxaquadricyclane, oxanorbornadiene, and relatedcompounds with cyclooctyne, HETEROCYCLE, 49, 1998, pp. 79-83
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
49
Year of publication
1998
Pages
79 - 83
Database
ISI
SICI code
0385-5414(199812)49:<79:CROOOA>2.0.ZU;2-D
Abstract
Dimethyl oxaquadricyclane-2,3-dicarboxylate (1) with cyclooctyne (CO) gave, via carbonyl ylide (3a), a mixture of the exo and endo 1:1 adducts (2a, 2b ) along with the novel 1:2 adduct (2c), whereas the carbocyclic analogs und erwent [sigma 2s + sigma 2s + pi 2s]cycloaddition. The first examples of in verse electron demand homo-Diels-Alder reactions of oxa-, aza- and carbo-no rbornadienes with CO were also described.