Synthesis of 2‐silaoxane via 1,3‐ photocycloaddition | Zendy

Bahu Suhail | Zendy; Fleming Steven A. | Zendy; Nilsson Brad | Zendy; Turner Tim | Zendy

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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.

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