TY - JOUR
T1 - Phenyl Migration in Pseudohalogen Additions to 3,3,3-Triphenylpropene
AU - Hassner, Alfred
AU - Teeter, J. S.
PY - 1970/10/1
Y1 - 1970/10/1
N2 - Addition of iodine azide (IN3) to tritylethylene (1), unlike to i-butylethylene, leads to complete rearrangement producing 3-azido-2,3,3-triphenyl-1-propyl iodide (2) in 90% yield. Treatment of 2 with potassium t-butoxide gave triphenylacrolein. Under milder conditions it was possible to isolate an intermediate allylic azide. A rearranged product was also noted on iodine isocyanate addition to 1. Similarly, benzonorbornadiene gave a 1,3 adduct resulting from a Wagner-Meerwein phenyl migration and methylenenorbornene produced a rearranged IN3 adduct.
AB - Addition of iodine azide (IN3) to tritylethylene (1), unlike to i-butylethylene, leads to complete rearrangement producing 3-azido-2,3,3-triphenyl-1-propyl iodide (2) in 90% yield. Treatment of 2 with potassium t-butoxide gave triphenylacrolein. Under milder conditions it was possible to isolate an intermediate allylic azide. A rearranged product was also noted on iodine isocyanate addition to 1. Similarly, benzonorbornadiene gave a 1,3 adduct resulting from a Wagner-Meerwein phenyl migration and methylenenorbornene produced a rearranged IN3 adduct.
UR - http://www.scopus.com/inward/record.url?scp=0010735620&partnerID=8YFLogxK
U2 - 10.1021/jo00835a046
DO - 10.1021/jo00835a046
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AN - SCOPUS:0010735620
SN - 0022-3263
VL - 35
SP - 3397
EP - 3401
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -