1-Isopropyl-4-methylenebicyclo[3.1.0]hex-2-ene. Synthesis and reactions

Chung, Ryan; Lin, Grace J.; Nicholson, Jesse M.; Tseng, Anna; Tucker, Ozie; Wheeler, J. W.

doi:10.1021/ja00762a004

Cited by 6 publications

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Cyclopropanes from Unsaturated Compounds, Methylene Iodide, and Zinc‐Copper Couple

et al. 2011

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The reaction of the organozinc reagent prepared from methylene iodide and zinc‐copper couple with substituted unsaturated compounds has proved to be a versatile and convenient method for the synthesis of cyclopropanes. The synthesis is stereospecific with regard to the stereochemistry of the unsaturated compound and is usually free from serious side reactions; it can be carried out under mild conditions in diethyl and affords cyclopropanes often in good yields. This method can be easily adapted to large‐scale preparations. Two useful variations of the cyclopropanation reaction have appeared which involve the same or a similar organozinc intermediate: (1) diazomethane reacts with iodide in ether to form a reagent which converts unsaturated compounds to cyclopropanes; (2) methlyene iodide and diethyl zinc react in ether in the presence of unsaturated compounds to cyclopropanes. Processes are known in which a divalent carbon fragment adds to carbon‐carbon double bonds either as a free carbene or as an organometallic complex.

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Cyclopropanes from Unsaturated Compounds, Methylene Iodide, and Zinc‐Copper Couple

et al. 2011

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ChemInform Abstract: 1‐ISOPROPYL‐4‐METHYLEN‐BICYCLO(3,1,0)HEXEN‐(2), SYNTH. UND RK.

Chung¹,

Lin²,

Nicholson³

et al. 1972

Chemischer Informationsdienst

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An Anomalous Oxidation of β‐Pinene

Jefford

Roussel

Evans

1975

Helvetica Chimica Acta

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The oxidation of β‐pinene with aqueous alkaline potassium periodate and catalytic amounts of potassium permanganate gave, in addition to the expected oxidation product nopinone, a β‐ketol. The structure of the latter was shown to be 1‐(2‐hydroxyisopropyl)bicyclo[3.1.0]hexan‐2‐one. The formation of this anomalous side‐product represents a new type of rearrangement of the pinane skeleton.

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1-Isopropyl-4-methylenebicyclo[3.1.0]hex-2-ene. Synthesis and reactions

Cited by 6 publications

References 1 publication

Cyclopropanes from Unsaturated Compounds, Methylene Iodide, and Zinc‐Copper Couple

Cyclopropanes from Unsaturated Compounds, Methylene Iodide, and Zinc‐Copper Couple

ChemInform Abstract: 1‐ISOPROPYL‐4‐METHYLEN‐BICYCLO(3,1,0)HEXEN‐(2), SYNTH. UND RK.

An Anomalous Oxidation of β‐Pinene

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