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Hetero‐ Diels‐Alder Cycloadditions of α , β ‐Unsaturated Acyl Cyanides, Part 4, Substituent Effects in Reactions with p ‐Substituted Styrenes
Author(s) -
Zhuo JinCong,
Wyler Hugo
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990707)82:7<1122::aid-hlca1122>3.0.co;2-d
Subject(s) - chemistry , substituent , styrene , cycloaddition , medicinal chemistry , concerted reaction , reaction rate constant , aryl , pyran , organic chemistry , kinetics , catalysis , physics , alkyl , quantum mechanics , copolymer , polymer
Cycloadditions of α , β ‐unsaturated acyl cyanides (=2‐oxonitriles) 1 – 6 to styrene and its p ‐substituted derivatives 7a – f , h are of inverse electron demand and provide, under mild conditions, regio‐ and stereoselectively 2‐aryl‐3,4‐dihydro‐2 H ‐pyran‐6‐carbonitriles 8 – 13 , generally in good yield. Rates for the cycloaddition of acryloyl cyanide 1 to p ‐substituted styrenes, determined in competition reactions of substrate pairs relative to that of styrene, increase in the order of electron‐donating ability NO 2