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

doi:10.1021/jo00321a030

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

^*Corresponding author for this work

School of Chemistry

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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 language	English
Pages (from-to)	1673-1679
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	46
Issue number	8
DOIs	https://doi.org/10.1021/jo00321a030
State	Published - Apr 1981

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title = "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)",

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.",

author = "Kosower, {Edward M.} and Barak Pazhenchevsky and Hanna Dodiuk and Marcia Ben-Shoshan and Hanna Kanety",

year = "1981",

month = apr,

doi = "10.1021/jo00321a030",

language = "אנגלית",

volume = "46",

pages = "1673--1679",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - 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)

AU - Kosower, Edward M.

AU - Pazhenchevsky, Barak

AU - Dodiuk, Hanna

AU - Ben-Shoshan, Marcia

AU - Kanety, Hanna

PY - 1981/4

Y1 - 1981/4

N2 - 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.

AB - 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.

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SN - 0022-3263

VL - 46

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

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)

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