Premium
[4.4.1]Propellatetraene and Related Propellanes
Author(s) -
Frauenrath Herbert,
Kapon Moshe,
Rubin Mordecai B.
Publication year - 1989
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198900040
Subject(s) - chemistry , isomerization , adduct , annulene , hydrolysis , propellane , computational chemistry , photochemistry , medicinal chemistry , organic chemistry , bicyclic molecule , catalysis
Reaction of dichlorovinylene carbonate with 1,6‐methano[10]annulene ( 2 ) followed by hydrolysis of the intermediate adduct afforded α‐diketone 3 . Photolysis of 3 at liquid nitrogen temperature yielded the title compound, 1 . The activation parameters for the thermal isomerization 1 → 2 were ΔH + = 5.1 kcal/mole and ΔS − = −19 eu (100 K). The structure of 3 was established by X‐ray analysis. This analysis and MM2 calculations on a number of related compounds provide additional examples of the so‐called “Klammer” effect in propellanes.