Part I. The Synthesis of 11-hydroxy-tricyclo [6.2.1.02,̳7] Undeca-3,5,9-tiene: Part II. A Study of the Phenylpropiolic Acid Cyclization |
Contents
Historical Background | 11 |
Synthetic Routes to Tricyclo6 2 1 0²7 | 16 |
The Simpler Route from 55Diethoxy | 22 |
14 other sections not shown
Common terms and phrases
7-norbornadienyl a-Pyrone absorption alcohol 54-S Amer anhydride antimony pentafluoride aqueous benzene benzoquinone bis-tosyl hydrazone bridgehead protons Calcd carbonium ion cation CH3O OCH3 Chem Chlorocarbonate Chlorocarbonate 62 chromatography cm¯¹ CN CN CN cooled cyclization cyclopentadiene diene diene-dione 33 Dimethoxy Triene 48 distilled endo addition ene-dione ether Figure filtration fluorosulfonic acid G. A. Olah H₂ HOMO hydrazone hydrolysis intermediate isomers ketone longicyclic low temperature LUMO methanol methylene chloride ml methylene chloride mmol molecular orbital multiplet nitrogen inlet nmr tube norbornadiene P. R. Story peak pentane phenylpropiolic acid pmr CDC13 Pmr Data pmr spectrum protons reaction Recrystallization removed by rotary ribbon room temperature rotary evaporation singlet solution spectra were obtained stirred sublimation sulfonic acid sulfur dioxide sulfuryl chloride fluoride synthesis Table tion topology torr triene triene 36 triene ketal 48 vacuum vinyl washed Winstein yellow oil yield