TY - JOUR
T1 - Practical synthesis and reactivity of [3]dendralene
AU - Bradford, Tanya A.
AU - Payne, Alan D.
AU - Willis, Anthony C.
AU - Paddon-Row, Michael N.
AU - Sherburn, Michael S.
PY - 2010/1/15
Y1 - 2010/1/15
N2 - (Chemical Equation Presented) Aconvenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diels-Alder reactivity of [3]dendralene - including double cycloaddition sequences and catalytic enantioselective variant - are reported.
AB - (Chemical Equation Presented) Aconvenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diels-Alder reactivity of [3]dendralene - including double cycloaddition sequences and catalytic enantioselective variant - are reported.
UR - http://www.scopus.com/inward/record.url?scp=75349102024&partnerID=8YFLogxK
U2 - 10.1021/jo9024557
DO - 10.1021/jo9024557
M3 - Article
SN - 0022-3263
VL - 75
SP - 491
EP - 494
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -