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Highly Strained Cage Compounds from a Fourfold Bridged Tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene
Author(s) -
Gleiter Rolf,
Pflästerer Georg,
Irngartinger Hermann
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260422
Subject(s) - diazomethane , chemistry , yield (engineering) , diene , epoxide , derivative (finance) , cyclobutene , stereochemistry , cage , bridged compounds , medicinal chemistry , crystallography , ring (chemistry) , organic chemistry , catalysis , physics , natural rubber , mathematics , combinatorics , financial economics , economics , thermodynamics
The fourfold bridged tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene derivative 3 reacts with diazomethane and m 1‐chloroperbenzoic acid ( m CPBA) to yield the monoadduct 5 in good and the bisadduct 4 in poor yield as well as the mono‐and bisepoxides 7 and 8 in good yields, respectively. Also the “mixed” product 6 is obtained. All five compounds are strained propellanes. The X‐ray crystallographic structure analysis of 8 reveals a distance of 2.812 Å between the epoxide rings.