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In organic chemistry, spiro compounds are compounds that have at least two molecular rings with only one common atom. The simplest spiro compounds are bicyclic (having just two rings), or have a bicyclic portion as part of the larger ring system, in either case with the two rings connected through the defining single common atom. The one common atom connecting the participating rings distinguishes spiro compounds from other bicyclics: from isolated ring compounds like biphenyl that have no connecting atoms, from fused ring compounds like decalin having two rings linked by two adjacent atoms, and from bridged ring compounds like norbornane with two rings linked by two non-adjacent atoms. Spiro compounds may be fully carbocyclic (all carbon) or heterocyclic (having one or more non-carbon atom). One common type of spiro compound encountered in educational settings is a heterocyclic one— the acetal formed by reaction of a diol with a cyclic ketone. The common atom that connects the two (or sometimes three) rings is called the spiro atom; in carbocyclic spiro compounds like spiro[5.5]undecane (see image at right), the spiro-atom is a quaternary carbon, and as the -ane ending implies, these are the types of molecules to which the name spirane was first applied (though it is now used general of all spiro compounds). Likewise, a tetravalent neutral silicon or positively charged quaternary nitrogen atom (ammonium cation) can be the spiro center in these compounds, and many of these have been prepared and described. The 2-3 rings being joined are most often different in nature, though they, on occasion, be identical [e.g., spiro[5.5]undecane, just shown, and spiropentadiene, at right]. Although sketches of organic structures makes spiro compounds appear planar, they are not; for instance, a spiro compound with a pair of three-membered cyclopropene rings connected in spiro fashion (image below) has been given the popular misnomer of being a bow tie structure, when it is not flat or planar like a bow tie.

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Related publications (1)

Development of Catalytic Asymmetric C-H Functionalizations with Chiral Cyclopentadienyl Iridium(III) Complexes

Yun-Suk Jang

Cp*Ir(III) catalyzed C-H functionalization is a growing field, since it provides novel complementary reactivities, but enantioselective C-H functionalization reactions with this metal remain a niche. This thesis investigates CpXIr(III) catalyzed asymmetric, ortho-directed C-H functionalization reactions. While exploring an efficient enantioselective C-H amidation process, several chiral carboxylic acids were evaluated. A pronounced matched/ mismatched phenomenon between a chiral CpXIr(III) catalyst and (S)- and (R)-phthaloyl-tert leucine was found. This phenomenon was exploited to access highly enantioenriched P-chiral compounds. The corresponding phosphines are highly promising candidates as ligands for asymmetric catalysis. The enantioselective C(sp2)-H amidation of prochiral biaryl-phosphorus(V) compounds with various sulfonyl azides furnished the corresponding P-chiral products with up to 95% yield and up to 99:1 er. The cooperative system of CpXIr(III) and (S)-phthaloyl-tert leucine catalyzes a highly enantioselective C-H arylation reaction of phosphine oxides with ortho-quinone diazides. The catalytic reaction furnished the corresponding P-chiral phosphine oxides in up to 98% yield with 98.5:1.5 er. By using 1,2 diazonaphthol derivatives for the asymmetric C-H arylation reaction of phosphine oxides, a stable chiral axis was successfully implemented, giving access to P-chiral and axially chiral diastereomeric phosphorus(V) compounds with high selectivities and yields. Purely axially chiral phosphine oxides were also provided via an atropo-enantioselective C-H functionalization with up to 96:4 er and up to 95% yield. Additionally, chiral phosphorus(V) compounds were alkylated and reduced to their corresponding chiral phosphorus(III) compounds, without erosion of optical purity.

EPFL2019

Related concepts (7)

Ring (chemistry)

In chemistry, a ring is an ambiguous term referring either to a simple cycle of atoms and bonds in a molecule or to a connected set of atoms and bonds in which every atom and bond is a member of a cycle (also called a ring system). A ring system that is a simple cycle is called a monocycle or simple ring, and one that is not a simple cycle is called a polycycle or polycyclic ring system. A simple ring contains the same number of sigma bonds as atoms, and a polycyclic ring system contains more sigma bonds than atoms.

Spiro compound

Polycyclic compound

In the field of organic chemistry, a polycyclic compound is an organic compound featuring several closed rings of atoms, primarily carbon. These ring substructures include cycloalkanes, aromatics, and other ring types. They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), bridged compounds, and longifolene.

Related courses (3)

CH-335: Asymmetric synthesis and retrosynthesis

La première partie du cours décrit les méthodes classiques de synthèse asymétrique. La seconde partie du cours traite des stratégies de rétrosynthèse basées sur l'approche par disconnection.

CH-708: Frontiers in Organic Synthesis. Part II Synthesis of carbo- and hetero-cycles

See content

CH-120: Advanced general chemistry II

Acquisition des notions fondamentales liées à la réactivité des molécules organiques, identification de la structure de petites molécules organiques au moyen des techniques de spectrométrie de masse,

Related lectures (31)

Strategies for Macrocyclic Compounds Synthesis CH-335: Asymmetric synthesis and retrosynthesis

Covers strategies for the synthesis of macrocyclic compounds, focusing on DC disconnections and oxidation of alkenes.

Aromatic Compounds: Retrosynthesis Principles CH-335: Asymmetric synthesis and retrosynthesis

Covers the retrosynthesis of aromatic compounds, focusing on basic principles and the synthesis route.

Retrosynthesis Principles of Carbocyclic Compounds CH-335: Asymmetric synthesis and retrosynthesis

Covers retrosynthesis principles for carbocyclic compounds and selective reactivity of carbonyls and enolization.