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General experimental procedure
The reaction was carried out by simple addition of the organic
acid halide (1.1 mmol) to the cyclic ether (1.0 mmol) in a 10 mL
round-bottomed ask under solvent- and catalyst-free condi-
tions at rt. The reaction mixture was stirred at room tempera-
ture and monitored by TLC. Upon completion, the crude
mixture was diluted with EtOAc (5 mL) and washed with satu-
rated aqueous NaHCO3 (5 mL). The resulting solution was
extracted again with EtOAc (10 mL) and the combined organic
layers were dried over Na2SO4. The mixture was then concen-
trated in vacuo to yield the corresponding product. Column
chromatography was performed, if necessary, but generally the
products required no further purication.
Procedure for the preparation of acid iodide/acid bromides
The required acid iodides/acid bromides were prepared by
simple addition of 1.2 eq. NaI/LiBr to the corresponding acid
chlorides (1 eq.) in a 5 mL pear shaped ask and stirred for 10
min under closed vessel conditions at rt.11 When the acid
chlorides completely converted into acid iodides/acid
bromides, the colourless reaction mixtures (for acid iodides)
were turned to dark blackish yellow (for acid iodides)/reddish
yellow (for acid bromides). We have used these prepared acid
halides directly for the ring cleavage reactions with out
purication.
Acknowledgements
The authors are thankful to CSIR, New Delhi for the nancial
support and thankful to the Director, IICT for constant
encouragement. We express our deepest of gratitude and wish
to pay homage to our late mentor Dr Yenamandra Vekateswarlu
who passed away suddenly on July 17, 2013.
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