Convenient synthesis of ethyl (.+-.)-cis- and trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Klemmensen, Per D.; Kolind-Andersen, H.; Madsen, Hans Berg; Svendsen, Axel

doi:10.1021/jo01317a023

Cited by 18 publications

(4 citation statements)

References 2 publications

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“…The applicability of the protocol was further demonstrated in the synthesis of dichloroalkene 11 , which is a key intermediate in the synthesis of insecticide permethrin ( 12 ) (Scheme ). , The triethylborane-mediated trichloromethylation of cyclopropene 8 gave trichloromethylcyclopropane 9 , which underwent lactonization by treatment with concd. HCl to afford bicyclic compound 10 .…”

Section: Resultsmentioning

confidence: 99%

Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates

et al. 2016

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Reagent-controlled regiodivergent ring-opening reactions of trichloromethylcyclopropane carboxylates have been developed. The regioselectivity of bond cleavage is completely controlled by the proper choice of silver salts; the treatment of trichloromethylcyclopropane with AgBF4 led to C2-C3 bond cleavage and fluorination to afford fluorinated β,γ-unsaturated ester with high stereoselectivity, while the reaction with AgOAc in THF gave a γ,δ-unsaturated ester through the reductive cleavage of the C1-C2 bond.

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Section: Resultsmentioning

confidence: 99%

Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates

et al. 2016

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“…Minisci was amoung the first to observe that CCl 4 could be added to olefins to yield only the 1:1 adduct . Research has clearly shown that a variety of polyhalogenated compounds (alkyl halides, perfluoroalkyl iodides, and alkylsulfonyl chlorides) can be added across a CC bond. − Virtually any olefin can serve as the source of reactive unsaturation. The list of promoters is now quite extensive and includes powdered TM's or inorganic oxides; inorganic halides; 5d,,14a, mono-, , di-, and trinuclear metal carbonyls; cyclopentadienyl and arene complexes; ,, metal phosphine compounds; 8a,,− SmI 2 ; and RuCl 2 (PPh 3 ) 3 8a,27,28 or its polymer supported analogue …”

Section: Transition Metal Catalyzed Kharasch Additionmentioning

confidence: 99%

“…A few examples of these are shown in eqs 2-6. [5][6][7] Both inter-and intramolecular Kharasch addition 8 is possible.…”

Section: Introductionmentioning

confidence: 99%

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Diaminoarylnickel(II) “Pincer” Complexes: Mechanistic Considerations in the Kharasch Addition Reaction, Controlled Polymerization, and Dendrimeric Transition Metal Catalysts

1998

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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Convenient synthesis of ethyl (.+-.)-cis- and trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Cited by 18 publications

References 2 publications

Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates

Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates

Diaminoarylnickel(II) “Pincer” Complexes: Mechanistic Considerations in the Kharasch Addition Reaction, Controlled Polymerization, and Dendrimeric Transition Metal Catalysts

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

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