Dehydrohalogenation of Halo- and Dihalocyclopropanes

Osborn, C. L.; Shields, T. C.; Shoulders, Ben A.; Krause, J.; Cortez, H. V.; Gardner, Pete D.

doi:10.1021/ja01092a027

Cited by 34 publications

(12 citation statements)

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“…Melting and boiling points are uncorrected. Elemental analysis was performed by Galbraith Laboratories, Inc., Knoxville, Tenn. 9.9-DichIorobicyclo[6.1.0]non-4-ene (28). 1,5-Cyclooctadiene (54 g) and 65 g of chloroform were cooled to 10 °C.…”

Section: Discussionmentioning

confidence: 99%

Mechanism of olefin rearrangements induced by iron carbonyls. Rearrangements in the bicyclo[6.1.0]nonene system

Barborak¹,

Dasher²,

McPhail³

et al. 1978

Inorg. Chem.

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Section: Discussionmentioning

confidence: 99%

Mechanism of olefin rearrangements induced by iron carbonyls. Rearrangements in the bicyclo[6.1.0]nonene system

Barborak¹,

Dasher²,

McPhail³

et al. 1978

Inorg. Chem.

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“…The azabicyclic compounds (39) and (40) formed in roughly equal amounts on photolysis of l-azidonorbornane in methanol could be derived from the primary ring-expansion products (41) and ( 4 2 ) by addition of methanol. However, the authors[""] favor a synchronous process that avoids these energy-rich intermediates.…”

Section: Unstable Compounds With S <mentioning

confidence: 99%

Bredt Compounds and the Bredt Rule

Köbrich

1973

Angew. Chem. Int. Ed. Engl.

133

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The Bredt rule, which proved useful in earlier decades mainly as an exclusion criterion in the assignment of structures, has in recent years become the stimulus for efforts to synthesize strained bicyclic systems with a bridgehead double bond. On the basis of the ring-strain forces operating in such systems, an extended Bredt rule is discussed. The "Bredt compounds" to which this rule applies, which include bicyclic systems not previously considered from this point of view (e. g. bridged methylenecyclopropanes), form a clearly circumscribed, interesting field within the chemistry of highly-strained hydrocarbons with ring unsaturation.

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“…Replacement of halogen by alkoxy and alkylthio groups has been achieved in some cases but is frequently accompanied by elimination. They are also formed by treatment of some halocyclopropanes with base, probably by way of cyclopropene intermediates (197)(198)(199) They are also formed by treatment of some halocyclopropanes with base, probably by way of cyclopropene intermediates (197)(198)(199) …”

Section: >=< + :Cxymentioning

confidence: 99%

Addition to Alkenes

Kirmse

1971

Carbene Chemistry

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Dehydrohalogenation of Halo- and Dihalocyclopropanes

Cited by 34 publications

References 0 publications

Mechanism of olefin rearrangements induced by iron carbonyls. Rearrangements in the bicyclo[6.1.0]nonene system

Mechanism of olefin rearrangements induced by iron carbonyls. Rearrangements in the bicyclo[6.1.0]nonene system

Bredt Compounds and the Bredt Rule

Addition to Alkenes

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