On the Distribution of Linear versus Angular Naphthalenes in Aromatic Tetradehydro‐Diels–Alder Reactions – Effect of Linker Structure and Steric Bulk

• Published in: European journal of organic chemistry Vol. 2017; no. 23; pp. 3381 - 3385
• Main Authors: Chinta, Bhavani Shankar, Baire, Beeraiah
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 23.06.2017; Wiley Subscription Services, Inc
• Subjects: Alkynes; Chemistry; Chemistry, Organic; Cycloaddition; Diels-Alder reactions; Enynes; Naphthalene; Physical Sciences; Science & Technology; Substituent effects; Diels-Alder reactions; REARRANGEMENT; PALLADIUM; Cycloaddition; Substituent effects; Enynes; BENZANNULATION REACTION; CONJUGATED ENYNES; Alkynes; 4+2 CYCLOADDITION REACTIONS; CYCLOAROMATIZATION; DIYNES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201700588

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. A systematic study on the aromatic tetradehydro‐Diels–Alder (Ar‐TDDA) reaction elucidates the effect of the structure of the linker and the steric bulk of the substituent on the distribution of linear and angular naphthalene products. The structure of the linker has a tremendous effect on the product distribution. The effect of steric bulk of the substituent is dependent on the linker structure.