Reactions of Alkynyldihaloboranes with 1,3-Dienes. 1,4-Alkynylborations and Stepwise Diels-Alder Reactions. Academic Article

abstract

• Alkynyldihaloboranes 1-6 are readily generated in situ from the boron-tin exchange reaction of BCl(3) or BBr(3) with the corresponding alkynylstannanes. The Diels-Alder reactions of 1-4 with isoprene in hexanes proceed rapidly at 25 degrees C, affording 1,4-cyclohexadiene products in high yield with high regioselectivity. Reactions carried out in CH(2)Cl(2) exhibited an alternative product that results from the formal 1,4-alkynylboration of the diene. The alkynylboration intermediates can undergo further conversion to the Diels-Alder adducts under the reaction conditions. The mechanism of these reactions is discussed.

authors

• Singleton, Daniel

author list (cited authors)

• Leung, S., & Singleton, D. A

citation count

• 32

complete list of authors

• Leung, Shun-Wang||Singleton, Daniel A

publication date

• January 1997

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Organic Chemistry  Journal

keywords

• 0305 Organic Chemistry

PubMed Central ID

• 11671495

Digital Object Identifier (DOI)

• 10.1021/jo961892h

start page

• 1955

end page

• 1960

volume

• 62

issue

• 7

URL

• http%3A%2F%2Fdx.doi.org%2F10.1021%2Fjo961892h