Concise synthesis of novel oxa-bridged compounds

Khan, Faiz Ahmed ; Dash, Jyotirmayee ; Sudheer, Ch. ; Sahu, Nilam ; Parasuraman, Karuppasamy (2005) Concise synthesis of novel oxa-bridged compounds Journal of Organic Chemistry, 70 (19). pp. 7565-7577. ISSN 0022-3263

Full text not available from this repository.

Official URL:

Related URL:


A stereoselective strategy for the replacement of the 1,2-dihaloalkene bridge of tetrahalonorbornyl derivatives by an oxygen bridge involving stepwise controlled oxidation, cleavage of the dione thus formed, and reiterative intramolecular SN2 displacement of two bridgehead halogens is devised. The synthesis of four highly strained pentacyclic bis-oxa-bridged derivatives 10, 27, 28, and 29 with interesting structural variations is presented. The two oxa bridges are syn to each other, separated by central cyclohexane and cycloheptane rings in 10 and 27, while they are anti to each other and are separated by central cyclopentane and furan rings in 28 and 29. In the case of the highly symmetric bis-oxa-bridged derivative 10 the two syn oxa bridges constrain the central cyclohexane ring into the boat form. The endo,anti,endo 2:1 bis adducts of 1,2,3,4-tetrahalo-5,5-dimethoxycyclopenta-1,3-diene with cyclopentadiene were prepared for the first time, while the reactivites of previously unexplored bis adducts derived from furan and cycloheptatriene were revealed.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:80339
Deposited On:31 Jan 2012 14:27
Last Modified:31 Jan 2012 14:27

Repository Staff Only: item control page