Eine stereospezifische Synthese von  syn ‐Bishomochinon über  p ‐Benzochinon‐bis(äthylen)ketal | Zendy

Heller Jürg E. | Zendy; Dreiding André S. | Zendy; O'Connor B. R. | Zendy; Simmons H. E. | Zendy; Buchanan G. L. | Zendy; Raphael R. A. | Zendy; Taylor R. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Eine stereospezifische Synthese von syn ‐Bishomochinon über p ‐Benzochinon‐bis(äthylen)ketal

Author(s) -

Heller Jürg E.,

Dreiding André S.,

O'Connor B. R.,

Simmons H. E.,

Buchanan G. L.,

Raphael R. A.,

Taylor R.

Publication year - 1973

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.19730560117

Subject(s) - chemistry , methylene , ethylene , hydrolysis , halogenation , medicinal chemistry , ether , stereospecificity , stereochemistry , organic chemistry , catalysis

The bis(ethylene)ketal of p ‐benzoquinone ( 6 ) has been prepared from the bis(ethylene)ketal of cyclohexane‐1,4‐dione ( 3 ) by bromination with bromine in ether followed by dehydrobromination with potassium t ‐butoxide. Two intermediate dibromides ( 4 and 5 ) were isolated and their constitutions as well as their configurations determined from spectroscopic properties. Partial hydrolysis of 6 furnished the mono(ethylene)ketal of p ‐benzoquinone ( 9 ), which was converted stereospecifically to syn ‐bishomoquinone ( 2 ) by the double addition of sodium dimethylsulfoxonium‐methylide. The intermediate mono(ethylene)ketals of syn ‐bishomoquinone ( 11 ) as well as of the mono(methylene) addition product ( 10 ) were also isolated.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research