A simple method for preparing some cyclopropylcarbinyl compounds

✍ Scribed by Donald J. Peterson; M.Dwight Robbins

• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 181 KB
• Volume: 13
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)84787-0

✦ Synopsis

I&~ring the relatively recent past several cyclopropylcarbinyl derivatives have been prepared by a variety of procedures. The casmon basis for the most widely used of these methods formally involves additions of divalent carbon fragments fran precursors such as AllgcBr, IZnCIi2I,'&I~, and 8CW2 to ally1 caspounds. Although these methods have considerable utility, none of them, for one reason or another, can be regarded as the ultimate synthetic tool. ' Consequently, we now describe a method which fills sane of the need that currently exists fog improved and more versatile cyclopropylcarbinyl ccmpound syntheaee.

Our unique method very simply involves additions of electrophilic reagents (C12, Sr2, 12, so,, RSCl and @Cl,) to 3-butenyltributyltin to give directly in moderate to high yields the J c corresponding cyclopropylcarbinyl caupaunds. Bu3SnCJi2CH2CH-CE2 +I3 + ->Drxr,p + Bu3h+ 72 -86% I%+ -Cl +, Br+, I+ ,&-, BB+ and &Cl Three modes of electrophillc attack on the organotin caspcund are possible: (1) cleavage of a butyl-tin bond;:! (2) cleavage of the butenyl-tin bond; or (3) addition to the carboncarbon double bond. With the exception of the reactions of 3-butenyltrlbutyltin with iodine