Related Experiment Video
Updated: Aug 16, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Concise synthesis of novel oxa-bridged compounds
Faiz Ahmed Khan1, Jyotirmayee Dash, Ch Sudheer
1Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. faiz@iitk.ac.in
Abstract:
[structures: see text] 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 S(N)2 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.
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Structure and Nomenclature of Epoxides
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
