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C,C‐Double Bond Participation in the Acid‐Catalyzed Cyclization of 9 exo ‐Methyl‐ anti 10,11 ‐tricyclo[4.2.1.1 2,5 ]deca‐3,7‐diene‐9 endo , 10 endo ‐diol. Influence of Steric Compression on the Product Distribution
Author(s) -
Tombo Gerardo M. Ramos,
Chakrabarti Sarmistha,
Ganter Camille
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660325
Subject(s) - chemistry , double bond , protonation , intramolecular force , steric effects , medicinal chemistry , stereochemistry , diol , catalysis , nucleophilic substitution , nucleophile , acid catalysis , group (periodic table) , organic chemistry , ion
Acid treatment of 9 exo ‐methyl‐ anti 10,11 ‐tricyclo[4.2.1.1 2,5 ]deca‐3,7‐diene‐9 endo , 10 endo ‐diol ( 8 ) leads to the two isomeric pentacyclic ethers 7 and 9 by intramolecular nucleophilic substitution of a protonated OH‐group with participation of a C,C‐double bond. The higher steric compression in diol 8 on the side of the tertiary OH‐group at C(9) and the C(3), C(4)‐double bond, accounts for the preferred formation of 7 over 9 .