Bromination of 5-methoxyindane: Synthesis of new benzoindenone derivatives and ready access to 7H-Benzo[c]fluoren-7-one skeleton

Date

2008-01-01

Author

TUTAR, Ahmet
BERKİL AKAR, KIYMET
Hark, Richard R.
Balcı, Metin

Metadata

Show full item record

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

Item Usage Stats

98
views

0
downloads

The photobromination of 5-methoxyindane and 5-methoxyindanone was studied at both high and low temperatures. 1,2,3-Tribromo-6-methoxyindene was easily synthesized by photolytic bromination of 5-methoxyindane at low temperature. 1,1,2,3-Tetrabromo-6-methoxyindene was obtained from the photobromination of 5-methoxyindan at 77 degrees C, which could then be easily converted to the 2,3-dibromo-6-methoxyindene by silver-supported hydrolysis. Photochemical bromination of 5-methoxy-1-indanone with N-bromosuccinimide (NBS) gave 3-bromo-6-methoxyindene, which upon thermolysis gave a benzo[c]fluorenone derivative.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/56905

Journal

SYNTHETIC COMMUNICATIONS

DOI

https://doi.org/10.1080/00397910801916223

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes Gueltekin, Demet Demirci; TAŞKESENLİGİL, Yavuz; DAŞTAN, Arif; Balcı, Metin (Elsevier BV, 2008-05-05) The low and high temperature bromination of 7-bromobicyclo[2.2.1]hept-2-ene and 2,7-dibromobicyclo[2.2.1]hept-2-ene were studied and the possible role of a neighboring group participation in rearrangements was investigated. The formation mechanism of the isomers as well as the role of the substituent on the rearrangement were discussed. The structure elucidation of the formed compounds was achieved by NMR spectral data; particularly, the gamma-gauche effect was discussed in connection with the configuration...
Uncatalyzed addition of TMSCN to acylphosphonates Demir, Ayhan Sıtkı; Reis, Omer; Kayalar, Metin; Eymur, Serkan; Reis, Barbaros (Georg Thieme Verlag KG, 2006-12-01) The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethyl-silyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.
Alkylation of l- and d-menthyl pentanoate with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane Demir, Ayhan Sıtkı (Informa UK Limited, 1996-01-01) The alkylation of l- and d-menthyl valerate with n-hexyl iodide and with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane gave modest levels of diastereoselection. The chirality of the ester group favoured slight degree of selectivity. The chiral centers had limited impact on diastereoselectivity.
ASYMMETRIC ENE REACTIONS OF 2-METHYLPROPENE WITH CHLOROALDEHYDES IN THE PRESENCE OF BORONTRIFLUORIDE-L-MENTHYLETHYL ETHERATE AKHMEDOV, IM; Tanyeli, Cihangir; AKHMEDOV, MA; MOHAMMADI, M; DEMIR, AS (Informa UK Limited, 1994-01-01) The asymmetric ene reactions of prochiral chloroaldehydes, chloral and 2,3-dichlorobutanal with 2-methylpropanal in the presence of BF3 l-menthylethyl etherate gave optically active homoallylic alcohols in 16-22% ee. The dechlorination of the chloro alcohols lead to the unsaturated derivatives of alcohols.
Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives Atlı, Selin; Tanyeli, Cihangir; Department of Chemistry (2005) a,β-Unsaturated cyclic ketones were selectively oxidized on a'- positions using Mn(OAc)3 and Pb(OAc)4, respectively. The resultant racemic a'-acetoxylated substrates were resolved into corresponding enantiomerically enriched a'-hydroxylated and a'-acetoxylated compounds via PLE hydrolysis. a'-Hydroxylated compounds are racemized quickly, so they were acetylated with acetyl chloride and pyridine in situ to give the corresponding a'-acetoxylated compounds. Resultant a'-acetoxy a,β-unsaturated cyclic ketones r...

Citation Formats

A. TUTAR, K. BERKİL AKAR, R. R. Hark, and M. Balcı, “Bromination of 5-methoxyindane: Synthesis of new benzoindenone derivatives and ready access to 7H-Benzo[c]fluoren-7-one skeleton,” SYNTHETIC COMMUNICATIONS, pp. 1333–1345, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56905.