Ring opening of some 1,1,2-trihalocyclopropanes with a polar substituent attached to C-2; evidence for regioselective attack directed by hydrogen bonding

Holmelid, Bjarte; Kvernenes, Ole H.; Hodne, Mari; Sydnes, Leiv K.

doi:10.3998/ark.5550190.0009.603

Cited by 8 publications

References 8 publications

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Phase Transfer Catalysis

Mąkosza

Fedoryński

2010

Encyclopedia of Catalysis

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Basic concept of phase transfer catalysis (PTC), specific features of this general methodology for executing organic reactions, and mechanism of catalytic action of PT catalysts are presented. Scope and limitations of application of PTC as a general tool of organic synthesis and advantages offered by this methodology are discussed. These discussions are illustrated by numerous examples of successful use of PTC in a variety of reactions of inorganic anions (substitution and addition reactions, β‐eliminations, oxidations, and reductions), heteroanions, and particularly carbanions (reactions with alkylating agents, carbonyl groups, activated carbon‐carbon multiple bonds, electrophilic arenes, heteroatom electrophiles) and carbenes. Possibility of use of PTC for reactions of metalloorganic compounds and complexes and for enantioselective reactions is discussed.

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Phase Transfer Catalysis

Mąkosza

Fedoryński

2010

Encyclopedia of Catalysis

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Semipinacol Rearrangement Induced by Cleavage of Dibromocyclopropane

et al. 2020

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A novel semipinacol rearrangement using dibromocyclopropanes as sources of carbocations was developed. Heating dibromocyclopropanes bearing a 1‐hydroxyalkyl group with silver perchlorate and 2,6‐lutidine induced cleavage of the cyclopropane ring to form allyl cations, which underwent 1,2‐shift of a substituent at the α‐position of the hydroxy group to give β,γ‐unsaturated carbonyl compounds having a quaternary carbon at the α‐position. Because the products have convertible functional groups such as bromo, vinyl, and formyl groups, the method is expected to be applicable to the synthesis of various molecules.

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Toward the Synthesis of Modified Carbohydrates by Conjugate Addition of Propane‐1,3‐dithiol to α,β‐Unsaturated Ketones

Valdersnes

Apeland

Flemmen

et al. 2012

Helvetica Chimica Acta

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Selected 5‐substituted derivatives 4 of 1,1‐diethoxy‐5‐hydroxypent‐3‐yn‐2‐one were treated with propane‐1,3‐dithiol under various conditions. The unprotected hydroxy ketones underwent cyclization during the dithiol addition and gave the corresponding 3‐(diethoxymethyl)‐2‐oxa‐6,10‐dithiaspiro[4.5]decan‐3‐ols 5 in 80–90% yield as the only products (Scheme 3 and Table 1). These products can be regarded as partly modified carbohydrates in the furanose form. When the benzyl‐protected analogues 10‐Bn of the 1,1‐diethoxy‐5‐hydroxypent‐3‐yn‐2‐one derivatives were treated with the same dithiol, however, no cyclization occurred; instead the corresponding 3‐{2‐[(benzyloxy)methyl]‐1,3‐dithian‐2‐yl}‐1,1‐diethoxypropan‐2‐one derivatives 11‐Bn were formed in good yield (up to 99%; Table 4). These 1,3‐dithianes were and are in the process of being converted to a number of new carbohydrate analogues, and here are reported high‐yield syntheses of functionalized molecules 17 belonging to the 5,5‐diethoxy‐1,4‐dihydroxypentan‐2‐one family of compounds (Table 7), via 15‐Bn (Table 5) and 16‐Bn (Table 6 and Scheme 8).

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Ring opening of some 1,1,2-trihalocyclopropanes with a polar substituent attached to C-2; evidence for regioselective attack directed by hydrogen bonding

Cited by 8 publications

References 8 publications

Phase Transfer Catalysis

Phase Transfer Catalysis

Semipinacol Rearrangement Induced by Cleavage of Dibromocyclopropane

Toward the Synthesis of Modified Carbohydrates by Conjugate Addition of Propane‐1,3‐dithiol to α,β‐Unsaturated Ketones

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