694-29-1

Basic information

• Product Name: cis-1-Cyclopentene-3,4-diol
• Synonyms: cis-1-Cyclopentene-3,4-diol
• CAS NO: 694-29-1
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• Mol File: 694-29-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cis-1-Cyclopentene-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-1-Cyclopentene-3,4-diol(694-29-1)
• EPA Substance Registry System: cis-1-Cyclopentene-3,4-diol(694-29-1)

Safety Data

• Hazardous Substances Data: 694-29-1(Hazardous Substances Data)

Upstream product

• 7129-41-1 6-oxabicyclo[3.1.0]hex-2-ene 
• 542-92-7 cyclopenta-1,3-diene 
• 100517-09-7 (+/-)-3t,4c-dibromo-cyclopentane-1r,2c-diol 

Downstream Products

• 876605-79-7 cis-1,2-bis-(toluene-4-sulfonyloxy)-cyclopentane 
• 802-56-2 cis-1.2-bis-phenylcarbamoyloxy-cyclopentane 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 911-73-9 (+/-)-cis-3,4-bis-(4-nitro-benzoyloxy)-cyclopentene 

Relevant articles and documents

Ring-fused gem-dibromocyclopropanes as precursors to enantiomerically pure D- and L-series 3-deoxy- and 2-amino-2,3-dideoxyaldohexose derivatives

The gem-dibromocyclopropanes that undergo silver(1)-promoted electrocyclic ring-opening and the resulting π-allyl cations trapped with a range of nucleophiles to give mixtures of cyclohexenyl bromides were discussed. It was found that the subjection of these products to ozonolytic cleavage afforded differentially protected and enantiopure D- and L-series 3-deoxy- and 2-amino-2,3-dideoxyaldohexoses. The results showed that monosaccharide derivatives, as well as related compounds were likely to prove useful as 'building blocks' in the construction of a range of carbohydrates.

Tandem ring opening-ring closing metathesis of cyclic olefins

Ruthenium alkylidene 1 has been utilized in the tandem ring opening-ring closing metathesis of cyclic olefins. This reaction produces a bicyclic molecule from a cyclic olefin. Reactivity is dependent upon strain, and thus ring size, in the substrate molecules. Competing oligomerization is observed in substrates having low ring strain; this process is inhibited by increasing dilution of the reaction or by adding alkyl substitution to the acyclic olefins.

Vinyl Epoxide Hydrolysis Reactions

The rates of hydrolysis of cyclopentadiene oxide (3), cyclohexadiene oxide (4), cycloheptadiene oxide (5), cyclooctadiene oxide (6), butadiene oxide (7), and styrene oxide (8) have been determined as a function of pH.Each epoxide exhibited acid-catalyzed hydrolysis at low pH, and 3-5 showed significant rates for "spontaneous" reaction with solvent at intermediate pH values.The hydrolyses of several of the vinyl epoxides (4 and 5) showed kinetic terms in HO- at pH > ca. 13.Specific chloride effects attributed to nucleophilic addition of Cl- to neutral epoxide were observed for those compounds (3, 4, and 8) hydrolyzed in KCl solutions.From kinetic and product studies, mechanisms for hydrolyses of the vinyl epoxides are postulated.Acid-catalyzed hydrolyses of 3, 4, 5, and 6 were found to be A-1 in nature, proceeding via intermediate allyl cations.Product distributions depended on the structure of the cation.Mechanisms and product distributions for the spontaneous hydrolyses of vinyl epoxides were found to be variable, and dependent on the structure of the epoxide.