Bimanes. 7. Synthesis and Properties of 4,6-Bridged syn-l,5-Diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones (µ-Bridged 9,10-Dioxabimanes)

Edward M. Kosower, Barak Pazhenchevsky, Hanna Dodiuk, Marcia Ben-Shoshan, Hanna Kanety

Research output: Contribution to journalArticlepeer-review

Abstract

The reaction of syn-4,6-bis(bromomethyl)-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones with appropriate difunctional nucleophiles leads to 4,6-bridged syra-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones (µ-bridged 9,10-dioxabimanes), in which the bridging atoms are carbon, nitrogen, and sulfur. Substituents on the bridging atoms include the following: (a) (on carbon) H, COOCH3, H, COOH, (COOCH3)2 (COOC2H6)2, (CN)2; (b) (on nitrogen) H, OH, COCH3, CH3, C2H5, (CH3)3C, CH2CH2OH, C(CH2OH)3, C(CH2OH)n(CH2OCOR)3-n (n = 0,1, 2; R = CH3, C15H31, C11H23), C(CH2OH)(CH2OC(CH3)2OCH2, (CH3)2+, C6H4X (X = H, CH30, CH3, CN, Br, Cl, COOC2H5), (CH3)(C6H4X)+ (X = CH3, Cl); (c) (on sulfur) none, CH3+, O2.

Original languageEnglish
Pages (from-to)1673-1679
Number of pages7
JournalJournal of Organic Chemistry
Volume46
Issue number8
DOIs
StatePublished - Apr 1981

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