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On the Distribution of Linear versus Angular Naphthalenes in Aromatic Tetradehydro‐Diels–Alder Reactions – Effect of Linker Structure and Steric Bulk
Author(s) -
Chinta Bhavani Shankar,
Baire Beeraiah
Publication year - 2017
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.201700588
Subject(s) - steric effects , chemistry , linker , substituent , naphthalene , product distribution , enyne , diels–alder reaction , steric factor , stereochemistry , computational chemistry , organic chemistry , catalysis , computer science , operating system
We report here a systematic study of the aromatic tetradehydro‐Diels–Alder (Ar‐TDDA) reaction to elucidate the factors that have significant effects on the distribution of linear and angular naphthalene products. Two factors were studied, that is, the nature of the linker and the steric bulk of the substituent of the enyne part. The structure of the linker has a tremendous effect on the product distribution. The effect of the steric bulk of the substituent is dependent on the linker structure, in other words, different preferences are observed for different linkers.