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Class of organic compounds with three rings sharing a single carbon bond
In organic chemistry, propellane is any member of a class of polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing
Propellane
Highly-strained hydrocarbon ring compound
[1.1.1]Propellane is an organic compound, the simplest member of the propellane family. It is a hydrocarbon with formula C5H6 or C2(CH2)3. The molecular
1.1.1-Propellane
Chemical compound
derived from [3.3.1]propellane by addition of a methylene bridge between the two larger rings. Like other small-ring propellanes, this compound is substantially
1,3-Dehydroadamantane
Chemical compound
[2.2.2]Propellane, formally tricyclo[2.2.2.01,4]octane is an organic compound, a member of the propellane family. It is a hydrocarbon with formula C8H12
2.2.2-Propellane
Chemical compound
to make [1.1.1]propellane. Conversely, some substituted bicyclo[1.1.1]pentanes are best synthesized from the corresponding propellanes. The bicyclo[1
Bicyclo(1.1.1)pentane
American chemist (1927–2026)
preparation of highly strained organic compounds bicyclobutane and [1.1.1]propellane: Wiberg died in Needham, Massachusetts, on May 10, 2026, at the age of
Kenneth_B._Wiberg
Proposed class of chemical bonds
central bond between the inverted tetrahedral carbon atoms in [1.1.1]propellanes. Theoretical calculations on a range of molecules have indicated that
Charge-shift_bond
Central atom with four substituents located at the corners of a tetrahedron
displaying inverted tetrahedral geometry are the smallest propellanes, such as [1.1.1]propellane; or more generally the paddlanes, and pyramidane ([3.3.3
Tetrahedral molecular geometry
Tetrahedral_molecular_geometry
Instability in molecules with bonds at unnatural angles
cyclopropanes, cyclopropenes, cyclobutanes, cyclobutenes, [1,1,1]propellanes, [2,2,2]propellanes, epoxides, aziridines, cyclopentenes, and norbornenes. These
Ring_strain
Polycyclic hydrocarbon
spontaneous polymerization of [1.1.1]-propellane C5H6 or C2(=CH2)3. In the reaction, the axial C-C bond of the propellane (the "bridge") is broken, creating
Staffane
Index of chemical compounds with the same molecular formula
Cyclooctadienes 1,3-Cyclooctadiene 1,5-Cyclooctadiene Cyclooctyne [2.2.2]Propellane [4.1.1]Propellane 4-Vinylcyclohexene This set index page lists chemical structure
C8H12
Organic chemical reaction
synthesis of ketonic compounds of the pentalane, [3,3,3]- and [4,3,3]-propellane series". Tetrahedron Letters. 9 (47): 4885. doi:10.1016/S0040-4039(00)72784-5
Knoevenagel_condensation
[1.1.1]Propellane
List of chemical compounds with unusual names
List_of_chemical_compounds_with_unusual_names
Chemical compound
contains four fused cyclopropane rings that form the faces of a tetrahedron Propellane contains three cyclopropane rings that share a single central carbon-carbon
Cyclopropane
Index of chemical compounds with the same molecular formula
3-Cycloheptadiene 1,4-Cycloheptadiene Cycloheptyne Norbornene [2.2.1]Propellane [3.1.1]Propellane This set index page lists chemical structure articles associated
C7H10
Chemical compound
trimethylenemethane Fe(η4-C(CH2)3)(CO)3. It is also a precursor to [1.1.1]-propellane. Mooradian, Aram; Cloke, J. B. (June 1945). "The Synthesis of
1,1-Bis(chloromethyl)ethylene
Chemical compound
bicyclobutane derivative. Propalene (Bicyclobutadiene) Bicyclopentane 1.1.1-Propellane Wiberg, K. B.; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler
Bicyclobutane
Chemical compound
structure; however, the name "iceane" has precedence. Adamantane Twistane Propellane Hexanitrohexaazaisowurtzitane Hamon, D. P. G.; Taylor, G. F. (1976). "A
Iceane
formula is therefore C2+m+n+o+pH2(m+n+o+p). When p = 0, the compounds are propellanes. The best known paddlane is [1.1.1.1]paddlane which can be seen as a
Paddlane
Chemical compound
20]icosane. In carbon skeleton of pagodane, there can be distinguished many propellane-type fragments. The overall synthesis can be summarized as follows: The
Pagodane
Index of chemical compounds with the same molecular formula
may refer to: TH-dimer, or tetrahydromethylcyclopentadiene dimer [4.3.3]Propellane This set index page lists chemical structure articles associated with
C12H20
Index of chemical compounds with the same molecular formula
66.04695 u) may refer to: Cyclopentadiene Cyclopropylacetylene [1.1.1]propellane Cyclopentyne This set index page lists chemical structure articles associated
C5H6
Class of chemical compounds
tricyclic molecules that are fused to a common central bond. Unlike the propellanes, the central bond is a transannular dative bond from a Lewis base—typically
Atrane
Elastic potential energy gained by a material under tensile or compressive stress
Compounds with unusually large strain energy include tetrahedranes, propellanes, cubane-type clusters, fenestranes and cyclophanes. March's Advanced
Strain_energy
Chemical reaction
Ramberg–Baecklund rearrangement as a synthetic entry to unsaturated propellanes". Journal of the American Chemical Society. 93 (18): 4516–4522. Bibcode:1971JAChS
Ramberg–Bäcklund_reaction
Named reaction for synthesis of organic halides
Cristol-Firth modification. The 1,3-dihalocyclobutanes were key precursors to propellanes. The reaction has been applied to the preparation of ω-bromo esters with
Hunsdiecker_reaction
French chemist (born 1955)
Bioisosteres of Internal Alkynes and para ‐Disubstituted Benzenes from [1.1.1]Propellane". Angewandte Chemie International Edition. 56 (41). Wiley: 12774–12777
Paul_Knochel
moieties to serve as building blocks in medicinal chemistry. Derivatives of propellane with reactive functional groups, such as the hydrochloride salt of 3-fluorobicyclo[1
Radical_fluorination
tetrafluorothiophene dioxide, octafluorotricyclooctadiene, a highly reactive propellane, tetrafluorocyclopentadienone, octafluorocyclooctatetraene, a heptafluorotropylium
David_M._Lemal
American chemist
Search: Award#1057143 – CAREER: New Strategies and Methods for the Total Synthesis of Propellane Natural Products". www.nsf.gov. Retrieved 2018-07-29.
Sarah_E._Reisman
Overview of and topical guide to organic chemistry
Tetracenes Triphenylenes Polycyclic Compounds (Non-Aromatic) Cubanes Propellanes Polymers Copolymers Graft Polymers Polyphenolic Compounds Flavonoids
Outline_of_organic_chemistry
Chemical compound
Claisen rearrangement and enyne radical closure: Routes to triquinane and propellane systems and use in the synthesis of (±)-ceratopicanol". Journal of Organic
Bis(cyclopentadienyl)titanium(III) chloride
Bis(cyclopentadienyl)titanium(III)_chloride
Israeli research pioneer
Reactions, Weinheim: Verlag Chemie (Monographs in Modern Chemistry, v. 7), Propellanes: Structure and Reactions: sequel I (July 1975-December 1980), Haifa:
David_Ginsburg_(chemist)
PROPELLANE
PROPELLANE
PROPELLANE
PROPELLANE
Girl/Female
American, British, English, Greek, Irish, Spanish, Swedish
Fortress; Lark; Lovely Flower; Most Beautiful; Variant of Cayley Lovely
Boy/Male
Arabic, Australian, Muslim, Sindhi
Equitable
Girl/Female
Greek
Violet flower. The name of a Gilbert and Sullivan Opera from 1882. Also a mythological sea nymph...
Boy/Male
Hindu
Fate
Boy/Male
Indian, Punjabi, Sikh
Heart Full of Love
Boy/Male
Hindu, Indian
Lord of Light
Boy/Male
Greek
Avenger.
Boy/Male
Indian, Kannada, Tamil
Word of God
Girl/Female
Arabic, Gujarati, Hindu, Indian, Kannada, Marathi, Muslim, Sanskrit
Dear
Female
English
Variant spelling of English Cheryl, probably SHARYL means "darling beryl."
PROPELLANE
PROPELLANE
PROPELLANE
PROPELLANE
PROPELLANE