Dipolar Cycloaddition Reactions with Heterocyclic Bicyclo[2.2.0]hexenes. – A Contribution to the  syn – anti  Selectivity of  cis ‐3,4‐Disubstituted Cyclobutenes | Zendy

Hassenrück Karin | Zendy; Höchstetter Hans | Zendy; Martin HansDieter | Zendy; Steigel Alois | Zendy; Wingen HeinzPeter | Zendy

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Dipolar Cycloaddition Reactions with Heterocyclic Bicyclo[2.2.0]hexenes. – A Contribution to the syn – anti Selectivity of cis ‐3,4‐Disubstituted Cyclobutenes

Author(s) -

Hassenrück Karin,

Höchstetter Hans,

Martin HansDieter,

Steigel Alois,

Wingen HeinzPeter

Publication year - 1987

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.19871200212

Subject(s) - chemistry , bicyclic molecule , cycloaddition , regioselectivity , selectivity , yield (engineering) , methylene , stereochemistry , medicinal chemistry , 1,3 dipolar cycloaddition , organic chemistry , catalysis , materials science , metallurgy

In order to examine the possible preference for anti or syn attack in bicyclic cyclobutenes, a series of heterocyclic bicyclo[2.2.0]hexenes, 3 – 8 , has been subjected to the reaction towards 1,3‐dipoles, particularly diazoalkanes. All dipolar cycloadditions exclusively lead to anti ‐configurated tricyclic products with varying regiochemistry in the cases of 4 – 8 . Similarly, the Pd‐catalyzed methylene transfer reactions only yield anti products. These results are in remarkable contrast to the known cycloaddition of, e.g., dichlorocyclobutene ( 1 ) or the carbonate 24 .

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