Premium
The Diels ‐ Alder Chemoselectivity of 3,4,6,7‐Tetramethylidenebicyclo[3.2.1]octane‐2‐ exo , 8‐ syn ‐diyl Derivatives
Author(s) -
Claret François,
Razaname Alain,
Vogel Pierre
Publication year - 1992
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/hlca.19920750412
Subject(s) - chemistry , moiety , octane , chemoselectivity , substituent , diene , medicinal chemistry , stereochemistry , organic chemistry , catalysis , natural rubber
Strong dienophiles prefer to add onto the diene moiety attached at C(2),C(3) of 2,3,6,7‐tetramethylidenebicyclo[3.2.1]octane ((±)‐ 1 ; see Scheme 1 ), whereas in the case of 3,4,6,7‐tetramethylidenebicyclo[3.2.1]octane‐2‐ exo ,8‐ syn ‐diyl derivatives, the diene moiety at C(6),C(7) reacts faster than that at C(3),C(4), as long the bulk of the 8‐ syn ‐substituent is large enough (see Schemes 2 and 3 ).
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom