57559-44-1

Upstream product

• 117468-09-4 (Z)-5,6-trans-dibromocyclooct-1-ene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 5259-72-3 cyclo-octa-1,5-diene 
• 24165-06-8 5,6-dibromo-1-cyclooctene 

Downstream Products

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 16538-84-4 (1E,5Z)-1-phenylcycloocta-1,5-diene 
• 1392323-39-5 C₂₁H₂₀BrNO 

Relevant academic research and scientific papers

1,5-Cyclooctadienyl alcohols and ketones generate a new class of COD Pt complexes

A variety of new racemic alcohol and ketone cyclooctadiene derivatives was prepared for their complexation with platinum to generate a new class of platinum(ii) complexes.

Expeditious Synthesis of Functionalized 1-Arylcyclooctadienes via Palladium-Catalyzed Lithium Cross-Coupling

The palladium-catalyzed direct cross-coupling of aryl bromides and (1Z,5Z)-cycloocta-1,5-dien-1-yllithium is described as an important method to synthesize 1-arylcyclooctadienes. The use of a well-established Pd2dba3/XPhos catalytic system affords the desired new compounds in good to excellent yields; the reaction proceeds at room temperature with both high efficiency and selectivity. Finally we found the best conditions to combine a suitable lithium-halogen exchange with a cross-coupling reaction. (Figure presented.).

Efficient synthesis of bicyclo[6.3.0]undecadienones by Nazarov cyclization/regioselective elimination

Easily accessible cyclooctadienyl vinyl ketones can generate fused bicyclic 8-5 (bicyclo[6.3.0]undecadienone) ring systems via the Nazarov cyclization when treated with Lewis acid. The resultant products contain three new stereocenters as well as olefins suitably situated to allow further structural elaboration. This concise sequence allows for the rapid preparation of intermediates that should be applicable to a variety of natural product targets containing this bicyclic core.

Cytotoxicity and NMR studies of platinum complexes with cyclooctadiene ligands

The synthesis of a series of platinum complexes containing cyclooctadiene ligands with the general structure PtMeL(R-cod) (where L = Cl, I, nC 3F7, iC3F7, nC8F 17, Me, aryl, alkynyl and R = H, Me, Et, iPr, nBu, iBu, nHex, Ph) is presented. All complexes are remarkably stable and were obtained in excellent yields. Their structure in both solution and the solid state were explored by crystal structures and multinuclear (1H, 13C, 19F, 195Pt) NMR spectroscopy. Cytotoxicity experiments with selected complexes in HeLa cells revealed higher toxicity in comparison to that of cisplatin for most of the structures.

Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis

A chiral anion phase-transfer system for enantioselective halogenation is described. Highly insoluble, ionic reagents were developed as electrophilic bromine and iodine sources, and application of this system to o-anilidostyrenes afforded halogenated 4H-3,1-benzoxazines with excellent yield and enantioselectivity.

A Simple Preparation of Cyclic Vinylic Bromides (1-Bromocycloalkenes and 1-Bromo-1,5-cyclooctadiene) from 1,2-Dibromocycloalkanes

1,2-Dibromocyclopentane, 1,2-dibromocyclohexane, 1,2-dibromocycloheptane, 1,2-dibromocyclooctane, 1,2-dibromocyclododecane, and 5,6-dibromocyclooctene are smoothly dehydrobrominated to the corresponding 1-bromocycloalkenes in good yield using morpholine and dimethyl sulfoxide in benzene or ethanol.

9-Oxabicyclononynes

Semiempirical quantum mechanics (MNDO) and force field calculations (MM 2) reveal that two diastereomeric conformations a and b of low energy exist for each of the three isomeric cis-9-oxabicyclononynes 1 - 3.Synthetically, the highly strained comp