5395-41-5

Upstream product

• 151694-33-6 2,2-dimethyl-1-phenylethynylcyclopropanol 
• 99824-96-1 pentacarbonyl[(methoxy)(2-phenylethynyl)carbene]chromium⁽⁰⁾ 
• 3017-69-4 2-methyl-1-propenylbromide 
• 497838-01-4 tert-Butyl-dimethyl-(2-methyl-1-phenylethynyl-propenyloxy)-silane 
• 151694-34-7 tert-Butyl-(2,2-dimethyl-1-phenylethynyl-cyclopropoxy)-dimethyl-silane 
• 5923-10-4 4-methyl-1-phenylpent-1-yn-3-one 
• 116053-66-8 1-Isopropylidene-3-phenyl-2-cyclobutene 
• 495414-15-8 (Z)-3-bromo-1-iodo-2-phenylpropene 
• 102934-89-4 (Z)-3-(trimethylsilyl)-3-iodo-2-phenyl-2-propen-1-ol 
• 495414-14-7 (E)-5-iodo-2,2-dimethyl-4-phenyl-4-pentenenitrile 

Relevant academic research and scientific papers

Surprising exocyclic regioselectivity in electrophilic additions to alkylidenecyclobutenes

The addition of peracid, bromine, TCNE and singlet oxygen to alkylidenecyclobutenes shows a strong regioselectivity - in some cases regiospecificity - for the exocyclic double bond. Depending on the reagent, the endocyclic double bond will only undergo reaction upon the addition of a second equivalent of reagent. In the case of the first three reagents, this exocyclic regioselectivity is rationalized by invoking the formation of the more stabilized carbocation intermediate or transition state. Regarding 1O2, where polar mechanisms are rare, we attribute this exocyclic regioselectivity to the improper alignment and, hence, lack of reactivity of the endocyclic allylic hydrogen.

Regio- and stereoselective synthesis of cyclopentenones: Intermolecular Pseudo-Pauson-Khand cyclization

Doing the two step: A very simple two-step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson-Khand reaction, and can be used wi

Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones

The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis. Copyright

Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds

An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)-propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.

Rearrangement of 1-(1-alkynyl)cyclopropanols to 2-cyclopentenones via their hexacarbonyldicobalt complexes. A new use of alkyne-CO2(CO)6 complexes in organic synthesis

A novel rearrangement of 1-(1-alkynyl)cyclopropanols to 2-cyclopenten- 1-ones proceeded on complexation of their alkynyl part with octacarbonyldicobalt (Co2(CO8)). 1-(1-Alkynyl)cyclopropanols with a wide range of substituents on thei

A Conformationally Controlled Regioselective of 2-Substituted 1-Alkynylcyclopropanols to 2-Cyclopenten-1-ones via Hexacarbonyldicobalt Complex

The rearrangement of hexacarbonyldicobalt-complexed 2-substituted 1-alkynylcyclopropanol derivatives is conformationally controlled to give 3- or 5-substituted 2-cyclopentanones regioselectively.In the cases of the reactions of 2-monosubstituted 1-alkynyl

Cyclocarbonylation of acyclic 1,3-dienes via their tricarbonyl iron complexes: Cyclopenten-2-ones and dicarbonyl cyclopentadienyl iron halides

Tricarbonyl iron complexes of acyclic 1,3-dienes can be converted to conjugated cyclopentenones by decomplexation with aluminium halides. Most complexes of simple dienes need drastic conditions for the cyclocarbonylation to occur (100 Atm CO, 100°C), with the exception of 1,1,3-trialkylbutadiene complexes which are nearly quantitatively converted into cyclopentenones at room temperature, even in the absence of a CO atmosphere. Under the same mild conditions, the other complexes lead in modest yields to cyclopentadienyl dicarbonyl iron halides by a cyclocarbonylation reaction followed by an aluminium halide promoted deoxygenation.