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Synthesis of 2‐silaoxane via 1,3‐ photocycloaddition
Author(s) -
Bahu Suhail,
Fleming Steven A.,
Nilsson Brad,
Turner Tim
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380615
Subject(s) - chemistry , cyclopentene , cycloaddition , alkene , ring (chemistry) , aryl , stereochemistry , silylation , tricyclic , diol , medicinal chemistry , organic chemistry , catalysis , alkyl
Irradiation of an aryl group with a silyl tethered alkene yields a tetracyclic 2‐silaoxane with high regiose‐lectivity. The multicyclic structure has been further modified to give an unstable tricyclic diol. Photocycloaddition between cyclopentene and phenylcyclopropane gave a single major cycloadduct without cyclopropyl ring opening, indicating that the putative radical intermediate involved in cycloaddition apparently has a very short lifetime if it exists at all.