1338795-56-4

Basic information

• Product Name: (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1338795-56-4
• Molecular Weight: 274.168
• Mol File: 1338795-56-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1338795-56-4)
• EPA Substance Registry System: (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1338795-56-4)

Safety Data

• Hazardous Substances Data: 1338795-56-4(Hazardous Substances Data)

Upstream product

• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 50874-13-0 1-methoxy-1-phenylpropyne 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

Formation of Cyclopropanes via Activation of (γ-Methoxy)alkyl Gold(I) Complexes with Lewis Acids

Treatment of the gold 3-methoxy-3-phenylpropyl complex (P)AuCH2CH2CH(OMe)Ph [P = P(t-Bu)2o-biphenyl] with AlCl3 at -78 °C led to the immediate (≤5 min) formation of a 4:1 mixture of phenylcyclopropane and (1-methoxypropyl)benzene in 86 ± 5% combined yield. Lewis acid activation of the stereochemically pure isotopomer erythro-(P)AuCH2CHDCH(OMe)Ph led to the formation of cis-2-deuterio-1-phenylcyclopropane in 84 ± 5% yield as a single stereoisomer, which established that cyclopropanation occurred with inversion of the γ-stereocenter. Similarly, ionization of the stereochemically pure cyclohexyl gold complex cis-(P)AuCHCH2CH(OMe)CH2CH2CH2 at -78 °C formed bicyclo[3.1.0]hexane in 82% ± 5% yield, which validated a low energy pathway for cyclopropanation involving inversion of the α-stereocenter. Taken together, these observations are consistent with a mechanism for cyclopropane formation involving backside displacement of both the Cγleaving group and the Cα (L)Au+ fragment via a W-shaped transition state.