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Highly Selective Electrophile‐Induced Cascade Reactions between o ‐Alkynylbenzaldehydes and Styrene Oxides Leading to the Formation of 1‐Naphthyl Ketones
Author(s) -
Patil Nitin T.,
Konala Ashok,
Singh Vipender,
Reddy Vaddu V. N.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900809
Subject(s) - chemistry , styrene , electrophile , aryl , iodine , naphthalene , enol , organic chemistry , ketone , medicinal chemistry , catalysis , alkyl , polymer , copolymer
An efficient method for the synthesis of naphthalene derivatives through reaction of o ‐alkynylbenzaldehydes and styrene oxides in the presence of molecular iodine was developed. The reaction involves Meinwald rearrangement of styrene oxides to form the corresponding aryl acetaldehydes. The enol forms of aryl acetaldehydes might undergo [4+2] benzannulation reactions with iodinated benzopyrilium ions, formed in situ from o ‐alkynylbenzaldehydes and iodine, to afford 1‐naphthyl ketones. The reaction was found to be highly selective, and of two possible products, only one was formed. Mechanistic aspects are discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)