5601-67-2

Basic information

• Product Name: 1,2-Cyclotridecadiene
• Synonyms: 1,2-Cyclotridecadiene
• CAS NO: 5601-67-2
• Molecular Formula: C₁₃H₂₂
• Molecular Weight: 178.31
• Mol File: 5601-67-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Cyclotridecadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclotridecadiene(5601-67-2)
• EPA Substance Registry System: 1,2-Cyclotridecadiene(5601-67-2)

Safety Data

• Hazardous Substances Data: 5601-67-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 23, p. 3645, 1967 DOI: 10.1016/0040-4020(67)80010-3

Upstream product

• 17301-57-4 13,13-dibromobicyclo<10.1.0>tridecane 
• 5601-66-1 cis-13,13-dibromobicyclo<10.1.0>tridecane 
• 5601-66-1 trans-13,13-dibromobicyclo<10.1.0>tridecane 
• 1501-82-2 cyclododecene 
• 6573-70-2 (E/Z)-cyclotridecene 

Downstream Products

• 56175-27-0 (E)-15,15-Dimethyl-bicyclo[11.2.0]pentadec-12-en-14-one 
• 56175-28-1 (Z)-15,15-Dimethyl-bicyclo[11.2.0]pentadec-12-en-14-one 
• 832-10-0 cyclotridecanone 
• 75805-78-6 (E)-13-Chloro-1-phenylselanyl-cyclotridecene 
• 133295-22-4 (Z)-20-(Toluene-4-sulfonyl)-20-aza-tricyclo[11.7.0.0^14,19]icosa-12,14⁽¹⁹⁾,15,17-tetraene 
• 30651-70-8 (3E,5E)-4,5-diethylocta-3,5-diene 
• 1258601-56-7 C₂₆H₄₆ 
• 1258601-79-4 3-(1-ethylbut-1-en-1-yl)cyclotridecene 

Relevant articles and documents

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Rhodium-Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3-Diketones

A rare case of a parallel kinetic resolution of racemic 1,3-disubstituted allenes by means of a rhodium-catalyzed addition to 1,3-diketones furnishing enantiopure allylic 1,3-diketones is described. Mechanistic experiments demonstrate that the different allene enantiomers react in parallel to either the diastereomeric E- or Z-allylic 1,3-diketones with the same absolute configuration of the newly formed stereogenic center. A broad substrate scope demonstrates the synthetic utility of this new method.

A three-carbon (n+1+2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis

The three-carbon ring expansion methodology commences with the preparation of a cyclic allene (C9, C11, C13), readily available from the corresponding cycloalkene via dibromocarbene addition and subsequent treatment with methyllithium. Dichloroketene addition to the cyclic allene regioselectively provides the [2+2] cycloadduct, which is reductively dechlorinated with zinc in methanol. The resulting cyclobutanone is then catalytically hydrogenated; cyclobutanone ring opening is affected with trimethylsilyl iodide; immediate dehydroiodination of the resulting β-iodocycloalkanone with diazabicycloundecane (DBU) provides the corresponding macrocyclic enone. The 15-membered enone was converted to d,l-muscone with (CH3)2CuLi.