Boron trifluoride mediated Prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols

Date

2006-05-03

Author

İŞLEYEN, ALPER
Doğan, Özdemir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

133
views

0
downloads

A one-pot procedure was developed for the synthesis of 3-chloro-3-arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported.

Subject Keywords

Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/37397

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-2006-926445

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols Şenocak, Deniz; Demir, Ayhan Sıtkı; Department of Chemistry (2004) Chiral cyclic alkenols with hydroxymethyl functionality are important structural units in many biologically active natural compouds such as prostaglandins, sesquiterpene antiviral agents, pentenomycins, xanthocidin, sarkomycin, etc. 1,3-cycloalkanediones are converted into bicyclic polyoxo derivatives with formaldehyde and trioxane in the presence of Lewis acid. Selective oxidation of the bicyclic compounds by using manganese(III)acetate followed by enzyme-catalyzed kinetic resolution afforded chiral bicycl...
Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes Dengiz, Çağatay; GUTIERREZ, Gregory D.; SWAGER, Timothy M. (American Chemical Society (ACS), 2017-07-21) The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels-Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF2, as observed by (HNMR)-H-1 analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels-Alder adduct 10 is additionally demonstrated and e...
Asymmetric synthesis of norbornene based 1,4-Aminoalcohol derivatives and applications in asymmetric diethylzinc reactions Erdem, Mine; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this result...
Bicyclic strained allenes : incorporation of an allene unit into alpha-pinene and benzonorbornadiene Kılbaş, Benan; Balcı, Metin; Department of Chemistry (2009) The synthesis of cyclic allenes with eight or less skeletal C-atoms, known as highly strained organic compounds, has for the past decades attracted increasing interest. The first part of study describes an investigation aimed at the incorporation of an allene unit into a natural compound, being α-pinene, by using β-elimination method. The two double-bond isomers 310 and 299b were synthesized as key compounds. Treatment of 310 with t-BuOK resulted in the formation of ketone 308 and diene 313. For the formati...
Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions Odabaş, Serhat; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrizati...

Citation Formats

A. İŞLEYEN and Ö. Doğan, “Boron trifluoride mediated Prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols,” SYNTHESIS-STUTTGART, pp. 1427–1432, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/37397.