Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes

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Title:Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes
Creators:
Czajkowski, David
Phillips, Oludotun A.
Reddy, Narender A. V.
Spevak, Paul
Lix, Bruce
Micetich, Ronald G.
Maiti, Samarendra N.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2352-2361

Abstract

The reactions of tert-butyl-3-acetoxymethyl-3-cephem-7-diazocephalosporanate 1,1-dioxide (<i>I</i>) with acetaldehyde, benzaldehyde, 2-thiophene caboxaldehyde, 3-thiophene carboxaldehyde, 2-furan carboxaldehyde, 3-furan carboxaldehyde and isobutyraldehyde have been studied. Use of boron trifluoride etherate as a catalyst for these reactions was found to accelerate the reactions markedly and to favour the formation of aldehydes rather than the ketones at C-7 position as the carbonyl product. The products obtained from these reactions and the ratios of carbonyl products to epoxides suggest that the R groups of the carbonyl component have profound influence on the reactions.

Title:Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes
Creators:
Czajkowski, David
Phillips, Oludotun A.
Reddy, Narender A. V.
Spevak, Paul
Lix, Bruce
Micetich, Ronald G.
Maiti, Samarendra N.
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2352-2361
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912352UNSPECIFIED
ID Code:5164
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Czajkowski, David; Phillips, Oludotun A.; Reddy, Narender A. V.; Spevak, Paul; Lix, Bruce; Micetich, Ronald G.; Maiti, Samarendra N. (1991) Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2352-2361. ISSN 0010-0765

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