113460-11-0

Basic information

• Product Name: Benzene, (2,2-dimethyl-3-pentenyl)-, (E)-
• CAS NO: 113460-11-0
• Molecular Formula: C13H18
• Molecular Weight: 174.286
• Mol File: 113460-11-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, (2,2-dimethyl-3-pentenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (2,2-dimethyl-3-pentenyl)-, (E)-(113460-11-0)
• EPA Substance Registry System: Benzene, (2,2-dimethyl-3-pentenyl)-, (E)-(113460-11-0)

Safety Data

• Hazardous Substances Data: 113460-11-0(Hazardous Substances Data)

Upstream product

• 50742-55-7 Tris-dimethylamino-aethyliden-phosphoran 
• 1009-62-7 2,2-dimethyl-3-phenylpropionaldehyde 
• 113460-16-5 C₂₇H₃₁OP 
• 67-56-1 methanol 
• 4736-60-1 ethyltriphenylphosphonium iodide 

Downstream Products

• 113460-15-4 trans-1-(1,1-dimethyl-2-phenylethyl)-2-methyloxirane 
• 113686-96-7 5-Ethyl-5-((1R,2S)-2-hydroxy-1,3,3-trimethyl-4-phenyl-butyl)-5H-dibenzophospholium; iodide 
• 113460-16-5 C₂₇H₃₁OP 

Relevant articles and documents

DBP YLDES: WITTIG REAGENTS FOR SYNTHESIS OF E-ALKENES FROM ALDEHYDES

Phosphorus yldes based on the dibenzophosphole (DPP) ring system convert aldehydes into trans-disubstituted oxaphosphetanes with good to excellent selectivity.Decomposition at 70-110 deg C affords alkenes with E:Z rations from 6:1 to > 100:1.

Stereochemistry of Carbenic 1,2-Vinyl Shifts

Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R′CH=CHC(Ph)=CR2, were found to predominate over γ-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R′ = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R′ = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).

A Bridged Tetrahydrophosphole Ylide Derived from 9-Phenylphosphabicyclononane: A Reagent for E-Selective Wittig Reactions

The bicyclic ylide 4 reacts with aldehydes to afford the E-alkenes.Selectivity is 94 - 6percent E for unbranched aldehydes, but the selectivity decreases with increasing α-branching.Ylide 4 is the first E-selective, nonstabilized ylide that allows efficient utilization of the P-alkyl substituent.

Mechanism of the Wittig Reaction: The Role of Substituents at Phosphorus

The variation in Wittig reaction stereochemistry is attributed to a dominant kinetic control in nearly all cases.Formation of cis or trans oxaphosphetanes is the decisive step, and this occurs by an asynchronous cycloaddition.An interplay of 1, 2 and 1, 3

Substituent Effects and the Wittig Mechanism: The Case for Stereospecific Oxaphosphetane Decomposition

A search for reversible Wittig reactions of the ylides a-d has been made by using the method of independent oxaphosphetane generation.Four pairs of diastereomeric oxaphosphetanes have been synthesized, and those corresponding to the Wittig reactions of b-