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- Title
Conformational Bias in Macrocyclic Ethers and Observation of High Solvolytic Reactivity at a Masked Furfuryl (=2-Furylmethyl) C-Atom.
- Authors
Guella, Graziano; Mancini, Ines; Öztunç, Aysel; Pietra, Francesco
- Abstract
New polyhalogenated, twelve-membered, O-bridged cyclic C15-ethers, having in common oxygenation at C(6) and a bromoallene side chain at C(4) (where C(1) is the bromoallene-chain terminus), were isolated from the red seaweed Laurencia obtusa from the Turkish Mediterranean Sea, i.e., the 9,12-O-bridged obtusallene VII ( 5), the 6,9 : 9,12-bis-O-bridged obtusallene V ( 3) and obtusallene VI ( 4), as well as the 6,9-O-bridged obtusallene VIII ( 8) and obtusallene IX ( 9). The behavior of portions of the macrocycle involved in fast motions and their equilibrium position depend on the particular compound, revealing a subtle conformational behavior of these macrocycles, while 8 and 9 show an unprecedented solvolytic reactivity at the masked furfuryl (=2-furylmethyl) C-atom.
- Publication
Helvetica Chimica Acta, 2000, Vol 83, Issue 2, p336
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/(SICI)1522-2675(20000216)83:2<336::AID-HLCA336>3.0.CO;2-R