16189-35-8

Basic information

• Product Name: CYCLOPENTYLIDENECYCLOPENTANE
• Synonyms: CYCLOPENTYLIDENECYCLOPENTANE;1,1'-bi(cyclopentylidene)
• CAS NO: 16189-35-8
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• Mol File: 16189-35-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -25-24 °C
• Boiling Point: 80 °C(Press: 16 Torr)
• Appearance: /
• Density: 0.8968 g/cm3(Temp: 420 °C)
• CAS DataBase Reference: CYCLOPENTYLIDENECYCLOPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPENTYLIDENECYCLOPENTANE(16189-35-8)
• EPA Substance Registry System: CYCLOPENTYLIDENECYCLOPENTANE(16189-35-8)

Safety Data

• Hazardous Substances Data: 16189-35-8(Hazardous Substances Data)

Upstream product

• 91011-88-0 1,1'-Dibromo-1,1'-bicyclopentane 
• 120-92-3 cyclopentanone 
• 5011-61-0 dispiro[4.1.4.1]dodecane-6,12-dione 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 34008-65-6 dicyclopentyl sulfone 
• 5181-75-9 bicyclopentyl-1,1'-diol 
• 65261-04-3 1-nitro-1-(1-nitrocyclopentyl)cyclopentane 
• 1528-30-9 methylenecyclopentane 
• 51175-23-6 11-oxa-dispiro[4.0.4.2]dodecan-12-one 
• 825-25-2 2-cyclopentylidenecyclopentan-1-one 

Downstream Products

• 311-38-6 6,7,13,14-tetraoxadispiro[4.2.4⁸.2⁵]tetradecane 
• 120-92-3 cyclopentanone 
• 13388-94-8 spiro[4.5]decan-6-one 
• 129731-35-7 6,12,13-Trioxadispiro<4.1.4.2>tridecan 
• 135084-70-7 1-(1-cyclopent-1-enylcyclopentyl)-4-phenyl-1,2-dihydro-1,2,4-triazole-3,5-dione 

Relevant articles and documents

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Salt/ligand-activated low-valent titanium formulations: the 'salt effect' on diastereoselective carbon-carbon bond forming SET reactions

A comprehensive study on the influence of exogenously added electropositive metal salts as promoters/secondary activators on preformed LVT species has resulted in the construction of highly efficient low-valent titanium (LVT) reagents. These salt-activated LVT reagents while exhibiting enhanced chemoselectivity and diastereoselectivity accelerated the reductive olefination rates of aromatic and aliphatic carbonyls under ambient temperature conditions and in much reduced reaction times. The versatility of the salted reagent was further explored in other single electron transfer reactions, namely, imino-pinacol couplings and one-pot synthesis of phenanthrenes from o-alkoxy aromatic carbonyls. We envisage that, in contrast to multiphase heterogeneous colloidal slurries, salt-activated LVT reagents afforded uniformly viscous homogeneous slurries generating a highly reactive monomeric intermetallic LVT complex. Continued judicious exploration of the emerging paradigms by studying the influence of external ligands/auxiliaries/redox agents on LVT reagents, and organometallics in general, will be critical to widen the scope and utility of the classical McMurry reaction and other SET reactions.

Activation of Low-Valent Titanium Reagents with Iodine: Facile Low-Temperature McMurry Reaction and N/O-Debenzylation/Deallylation

A highly reactive, low-valent titanium (LVT) reagent has been prepared by the addition of substoichiometric amounts of iodine to the LVT species generated by Rieke's method (TiCl3-Li-THF). While the conventional McMurry reaction requires high temperatures and prolonged reaction times for the generation of olefins, the present activated LVT reagent is able to effect the reductive coupling of aliphatic as well as aromatic carbonyls to the corresponding olefins at lower temperatures and much reduced reaction times. The protocol is also useful for the intramolecular coupling reactions leading to the one-step synthesis of heterocycles. The temperature-controlled McMurry reaction provides enhanced diastereoselectivity and features an excellent chemoselectivity. In addition to the McMurry reaction, other SET-induced carbon-heteroatom (O, N) bond cleavages can also be carried out with the activated reagent at a fast rate and at a low temperature in high yields.