SYNTHESIS OF 3-ARYL-5-CHLOROINDAN-1-ONES
423
1
(found in 3:1) for 265.0395, 267.0366; H NMR (300 MHz, CDCl3, d in ppm): 2.96
(1H, dd, J ¼ ꢂ16.5, 3.3 Hz, H2a), 3.21 (1H, dd, J ¼ ꢂ16.5, 10.2 Hz, H2b), 3.53 (1H,
dd, J ¼ 3.9, 3.6 Hz, H3), 6.74 (1H, d, J ¼ 8.4 Hz, H7), 7.11 (1H, dd, J ¼ 8.4, 2.1 Hz,
H6), 7.25–7.36 (6H, m, H4 & Ph prot0ons); 13C NMR (75 MHz, CDCl3, d in ppm):
0
38.9 (d, C3), 46.2 (t, C2), 123.5 (d, C4 ), 125.3 (d, C6), 129.7, 130.1 (2 ꢁ each, d, C2
0
0
& C3 ), 132.2 (d, C4), 134.5 (d, C7), 137.2 (s, C5), 138.4 (s, C7a), 139.2 (s, C1 ),
142.3 (s, C3a), 205.2 (s, C1).
CONCLUSION
The radical-mediated cyclization of enones has been successfully accomplished.
This strategy is a major breakthrough in the synthetic organic chemistry because it leads
to the constructions of 3-arylindan-1-ones 3a–d under neutral conditions; thus sub-
strates bearing functionalities that are vulnerable to acidic or alkaline medium can be
easily reacted under radical cyclization conditions without affecting functional groups.
ACKNOWLEDGMENTS
The authors are obliged to the Higher Education Commission, government of
Pakistan, for generous support of a research project (HEC 20-809), fellowship to
Aeysha Sultan (074-141-Ps4-435), and IRSIP award and financial assistance for ESI
MS, LR EIMS, and NMR analyses. The authors are also grateful to the Department
of Physics, University of Sargodha, for the single-crystal XRD facility.
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