Carbon Dioxide

Mander, Lewis N.

doi:10.1002/047084289x.rc011

Encyclopedia of Reagents for Organic Synthesis 2001

DOI: 10.1002/047084289x.rc011

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Carbon Dioxide

Lewis N. Mander¹

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2002

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“…The anions were then quenched. The electrophilic reagent carbon dioxide was bubbled in excess into the anion mixture over 5−15 min by warming of dry ice and passing the gas sequentially through dry calcium chloride and then concentrated sulfuric acid …”

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confidence: 99%

Complex-Induced Proximity Effects. Temperature-Dependent Regiochemical Diversity in Lithiation−Electrophilic Substitution Reactions of N-BOC-2-Azabicyclo[2.1.1]hexane. 2,4- and 3,5-Methanoprolines

et al. 2002

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[reaction: see text] Azabicycle 4 and sec-butyllithium/TMEDA afford the C(1) bridgehead alpha-lithio anion at 0 degrees C. Anion quenching with carbon dioxide, methyl chloroformate, or DMF provide the bridgehead acid 8a (N-BOC-2,4-methanoproline), ester 8b, or aldehyde 8c, respectively. By contrast, at -78 degrees C these same reagents give a mixture of regioisomeric methylene and bridgehead anions whose quenching leads to mixtures of regioisomeric methylene and bridgehead acids 6a/8a, esters 6b/8b, or aldehydes 6c/8c, respectively. The previously unknown 3,5-methanoproline was prepared as its N-BOC methyl ester 6b.

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confidence: 99%

Complex-Induced Proximity Effects. Temperature-Dependent Regiochemical Diversity in Lithiation−Electrophilic Substitution Reactions of N-BOC-2-Azabicyclo[2.1.1]hexane. 2,4- and 3,5-Methanoprolines

et al. 2002

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Carbon Dioxide

Cited by 1 publication

References 42 publications

Complex-Induced Proximity Effects. Temperature-Dependent Regiochemical Diversity in Lithiation−Electrophilic Substitution Reactions of N-BOC-2-Azabicyclo[2.1.1]hexane. 2,4- and 3,5-Methanoprolines

Complex-Induced Proximity Effects. Temperature-Dependent Regiochemical Diversity in Lithiation−Electrophilic Substitution Reactions of N-BOC-2-Azabicyclo[2.1.1]hexane. 2,4- and 3,5-Methanoprolines

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