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

TUTAR, Ahmet
Hark, Richard R.
Balcı, Metin
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.


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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.
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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.
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: