74437-39-1

Basic information

• Product Name: 2-Phenylnorbornadiene
• Synonyms: 2-Phenylnorbornadiene
• CAS NO: 74437-39-1
• Molecular Formula: C₁₃H₁₂
• Molecular Weight: 0
• Mol File: 74437-39-1.mol

Chemical Properties

• Boiling Point: 257.2°C at 760 mmHg
• Flash Point: 104.6°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 0.0237mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 2-Phenylnorbornadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylnorbornadiene(74437-39-1)
• EPA Substance Registry System: 2-Phenylnorbornadiene(74437-39-1)

Safety Data

• Hazardous Substances Data: 74437-39-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12/c1-2-4-11(5-3-1)13-9-10-6-7-12(13)8-10/h1-7,9-10,12H,8H2

Upstream product

• 115843-47-5 2-<(4-methylphenyl)sulphonyl>-3-phenyl-bicyclo<2.2.1>hepta-2,5-diene 
• 97760-26-4 2,3-bis(phenylsulfonyl)bicyclo[2.2.1]hepta-2,5-diene 
• 542-92-7 cyclopenta-1,3-diene 
• 123500-73-2 (1S,4R)-2-Benzenesulfonyl-3-phenyl-bicyclo[2.2.1]hepta-2,5-diene 
• 132555-54-5 5,6-Bis-benzenesulfonyl-5-chloro-bicyclo[2.2.1]hept-2-ene 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 
• 80188-19-8 Tetracyclo<3.2.0.0^2,7.0^4,6>hept-1-yllithium 
• 70887-53-5 1-Chlortetracyclo<3.2.0.0^2,7.0^4,6>heptan 
• 86660-93-7 1-Phenyltetracyclo<3.2.0.0^2,7.0^4,6>heptan 
• 141831-87-0 (1S,4R,6S)-5,5-Bis-benzenesulfonyl-6-phenyl-bicyclo[2.2.1]hept-2-ene 
• 134750-70-2 2-(2-Methyl-propane-2-sulfonyl)-bicyclo[2.2.1]hepta-2,5-diene 
• 123500-73-2 2-Benzenesulfonyl-3-phenyl-bicyclo[2.2.1]hepta-2,5-diene 

Downstream Products

• 74437-42-6 (1R,2R,4S,5S)-3,3-Difluoro-2-phenyl-tricyclo[3.2.1.0^2,4]oct-6-ene 
• 74437-54-0 C₁₄H₁₂F₂ 

Relevant articles and documents

Synthetic Equivalents to Substituted Acetylenes in Cycloaddition Reactions. Dienophilic Reactivity of 2-Methyl-, 2-Phenyl- and 2,3-Trimethylene-1,4-Benzodithiins-1,4-Tetroxides

Dienophiles 2-methyl-1,4-benzodithiin-1,4-tetroxide (3a), 2-phenyl-1,4-benzodithiin-1,4-tetroxide (3b) and 2,3-trimethylene-1,4-benzodithiin-1,4-tetroxide (3c) have been prepared with different methods starting from benzene-1,2-dithiol (1).Their reactivit

Alkyl- and arylsubstituted ketenedithioacetal tetroxides: Diels-Alder reactivity and reductive desulfonylation of the adducts

The Diels-Alder reactivity of the representative alkyl and aryl-substituted ketenedithioacetal tetroxides of general formula 1 is reported. These dienophiles reacted under thermal conditions (refluxing toluene) with cyclopentadiene to afford predominantly

BIS(TERT-BUTYLSULFONYL)ACETYLENE AS A GENERAL SYNTHETIC EQUIVALENT OF ALKYNES IN DIELS-ALDER CHEMISTRY. II: REDUCTIVE AND ALKYLATIVE DESULFONYLATIONS OF BICYCLIC 1-ALKYL-2-(TERT-BUTYLSULFONYL)ETHENES

Both reductive and alkylative desulfonylations of bicyclic vinyl sulfones derived from Diels-Alder cycloadducts of bis(tert-butylsulfonyl)acetylene (1) are described.These transformations establish the synthetic equivalence of 1 with acetylene, 1-alkynes

(Z)-AND (E)-1-CHLORO-1,2-BIS(PHENYLSULPHONYL)ETHYLENES: SYNTHONS OF BIS(PHENYLSULPHONYL)ACETYLENE AND OF TERMINAL ACETYLENES IN CYCLOADDITION REACTIONS

The cycloaddition reaction of both isomeric 1-chloro-1,2-bis(phenylsulphonyl)ethylenes 1 leads to the expected Diels-Alder adducts with a number of dienes.The (Z)-isomer is more reactive, but the adducts are dehydrochlorinated with more difficulty and in lower yields than the adducts derived from the cycloaddition of the (E)-isomer.The dehydrochlorinated products are bis(phenylsulphonyl)alkenes which formally derive from the cycloaddition of the hitherto unknown bis(phenylsulphonyl)acetylene.These compounds undergo addition-elimination reaction with Grignard reagents; the products, desulphonylated by sodium amalgam, can be considered as the Diels-Alder adducts of terminal acetylenes.

1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC SYNTHESIS: THE PREPARATION OF ALKYL- AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION - GRIGNARD REACTION - DESULFONYLATION SEQUENCE

A synthetic methodology for the preparation of the formal Diels-Alder cycloadducts of alkyl- and aryl-substituted acetylenes which exemplifies the utility of bis(phenylsulfonyl)alkenes 1 in organic synthesis is presented.The procedure entails -cycloaddition of (e)-1,2-bis(phenylsulfonyl)-1-chloroethylene (4), grignard reaction and desulfonylation; each step occurs in high yield.

REACTIVITY OF PHENYL(TOLYLSULFONYL)ACETYLENE TOWARDS DIENES AND HOMO-DIENES: CYCLOADDITIONS VERSUS FRAGMENTATION-ADDITION REACTIONS

Depending upon the diene, phenyl(tolylsulfonyl)acetylene (1a) affords the (4+2), the (2+2)-cycloadducts or products derived by 1,4-addition of the two fragments formed from homolytic cleavage of the carbon-sulfur bond.

Nucleophilic Exchange Reactions at 1-Chloroquadricyclane: 1,5- and 1,7-Dehydroquadricyclane as Reactive Intermediates.

Quadricyclane was metalated at position 1 to 1b in high yield by the complex of butyllithium and tetramethylethylenediamine or by a mixture of butyllithium and potassium tert-butoxide.Numerous 1-substituted quadricyclanes were accessible via 1b.Nuclophilic substitution products were obtained by the reaction of 1-chloroquadricyclane with organolithium compounds, lithium amides, and with lithium ethylthiolate (in the presence of a bulky strong base), which could be isomerized to the corresponding norbornadienes.Mechanistic investigations have shown that 1,7- and 1,5-dehydroquadricyclane (4 and 5) were involved as reactive intermediates.The nucleophilic substitution of optical active 1-chloroquadricyclane with lithium dimethylamide proceeded with 96percent racemization.This result is in accord with an elimination-addition mechanism passing over 4 and 5.